3-(4,5-Dihydroisoxazole-5-yl)benzoylpyrazole

ABSTRACT

The invention relates to 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of the formula (I) 
                         
wherein the variables are as defined herein. The invention also relates to the agriculturally useful salts thereof, to methods and to intermediate products for preparing the 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole, to agents containing them and to the use thereof for combating undesired plants.

This application is a 371 of PCT/EP00/12950 filed Dec. 19, 2000.

The present invention relates to3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I

where:

-   R¹, R² are hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl,    C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl;-   R³ is hydrogen, halogen or C₁–C₆-alkyl;-   R⁴ is hydrogen or C₁–C₄-alkyl;-   R⁵, R⁶ are hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, di(C₁–C₄-alkoxy)-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)amino-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)aminoimino-C₁–C₄-alkyl, hydroxyimino-C₁–C₄-alkyl,    C₁–C₆-alkoxyimino-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,    C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,    C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,    C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,    di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the two    last-mentioned substituents may be partially or fully halogenated    and/or may carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;        or-   R⁵ and R⁶ together form a C₂–C₆-alkanediyl chain which may be mono-    to tetrasubstituted by C₁–C₄-alkyl and/or may be interrupted by    oxygen or an unsubstituted or C₁–C₄-alkyl-substituted nitrogen;-   R⁷ is halogen, cyano, hydroxyl, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, amino,    C₁–C₆-alkylamino, di(C₁–C₆-alkyl)amino, di(C₁–C₄-alkoxy)methyl,    hydroxyimino-C₁–C₄-alkyl, C₁–C₆-alkoxyimino-C₁–C₄-alkyl or COR⁸;-   R⁸ is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, hydroxyl,    C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy, C₁–C₄-haloalkoxy,    C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy or NR⁹R¹⁰;-   R⁹ is hydrogen or C₁–C₄-alkyl;-   R¹⁰ is C₁–C₄-alkyl;-   R¹¹ is a pyrazole, attached in the 4-position, of the formula II

-   -   where    -   R¹² is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₃–C₆-alkenyl,        C₃–C₄-alkynyl, C₁–C₄-alkylcarbonyl, C₁–C₄-haloalkylcarbonyl,        C₁–C₄-alkylsulfonyl, C₁–C₄-haloalkylsulfonyl, thienylmethyl,        phenyl, benzyl, phenylcarbonyl, phenylsulfonyl or        phenylcarbonylmethyl, where the phenyl radical of the five        last-mentioned substituents may be partially or fully        halogenated and/or may carry one to three of the following        groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;    -   R¹³ is C₁–C₆-alkyl, C₁–C₆-haloalkyl or C₃–C₆-cycloalkyl;    -   R¹⁴ is hydrogen, C₁–C₆-alkyl or C₃–C₆-cycloalkyl;        and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates forpreparing compounds of the formula I, to compositions comprising themand to the use of these derivatives or of the compositions comprisingthem for controlling harmful plants.

Pyrazol-4-ylbenzoyl derivatives have been disclosed in the literature,for example in WO 96/26206.

However, the herbicidal properties of the prior-art compounds and theircompatibility with crop plants are not entirely satisfactory. It is anobject of the present invention to provide novel, in particularherbicidally active, compounds which have improved properties.

We have found that this object is achieved by the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I and bytheir herbicidal activity.

We have furthermore found herbicidal compositions which comprise thecompounds I and which have very good herbicidal activity. Moreover, wehave found processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they can exist asenantiomer or diastereomer mixtures. The present invention relates bothto the pure enantiomers or diastereomers and to the mixtures thereof.

The compounds of the formula I may also exist in the form of theiragriculturally useful salts, the type of salt generally being of noimportance. In general, suitable salts are the salts of those cations orthe acid addition salts of those acids whose cations, or anions,respectively, do not adversely affect the herbicidal activity of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, it beingpossible in this case, if desired, for one to four hydrogen atoms to bereplaced by C₁–C₄-alkyl or hydroxy-C₁–C₄-alkyl and/or a phenyl orbenzyl, preferably ammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, trimethylbenzylammonium, furthermore phosphoniumions, sulfonium ions, preferably tri(C₁–C₄-alkyl)sulfonium, andsulfoxonium ions, preferably tri(C₁–C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁–C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹–R¹⁵ or asradicals on phenyl rings are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,i.e. all alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxy,haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl,alkoxycarbonyl, haloalkoxycarbonyl, alkenyloxy, alkynyloxy, alkylamino,dialkylamino, alkoxyalkyl, dialkoxymethyl, dialkoxyalkyl,alkylthioalkyl, dialkylaminoalkyl, dialkylaminoiminoalkyl,hydroxyiminoalkyl, alkoxyiminoalkyl, alkoxycarbonylalkyl andalkoxyalkoxy moieties may be straight-chain or branched. Unlessotherwise specified, halogenated substituents preferably carry one tofive identical or different halogen atoms. The meaning of halogen is ineach case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁–C₄-alkyl and the alkyl moieties of C₁–C₄-alkylcarbonyl,        di(C₁–C₄-alkoxy)-C₁–C₄-alkyl,        di(C₁–C₄-alkyl)aminoimino-C₄-alkyl,        C₁–C₆-alkoxyimino-C₁–C₄-alkyl and hydroxyimino-C₁–C₄-alkyl: for        example methyl, ethyl, propyl, 1-methylethyl, butyl,        1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;    -   C₁–C₆-alkyl: C₁–C₄-alkyl as mentioned above and also, for        example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,        2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,        1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,        3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,        1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,        2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,        2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and        1-ethyl-3-methylpropyl;    -   C₁–C₄-haloalkyl and the haloalkyl moieties of        C₁–C₄-haloalkylcarbonyl: a C₁–C₄-alkyl radical as mentioned        above which is partially or fully substituted by fluorine,        chlorine, bromine and/or iodine, i.e., for example chloromethyl,        dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,        trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,        chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl,        1-chloroethyl, 1-bromomethyl, 1-iodoethyl, 2-fluoroethyl,        2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;    -   C₁–C₆-haloalkyl: C₁–C₄-haloalkyl as mentioned above and also,        for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,        5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl,        6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;    -   C₁–C₄-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-1-yl,        2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl,        3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl,        1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl,        4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,        1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,        2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and        2-cyanomethylprop-2-yl;    -   C₃–C₄-alkenyl: for example prop-1-en-1-yl, prop-2-en-1-yl,        1-methylethen-1-yl, buten-1-yl, buten-2-yl, buten-3-yl,        1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl,        1-methylprop-2-en-1-yl or 2-methylprop-2-en-1-yl;    -   C₃–C₄-alkynyl: for example prop-1-yn-1-yl, prop-2-yn-1-yl,        but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl or but-2-yn-1-yl;    -   C₁–C₄-alkoxy and the alkoxy moieties of di(C₁–C₄-alkoxy)methyl        and di(C₁–C₄-alkoxy)-C₁–C₄-alkyl: for example methoxy, ethoxy,        propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,        2-methylpropoxy and 1,1-dimethylethoxy;    -   C₁–C₆-alkoxy and the alkoxy moieties of        C₁–C₆-alkoxyimino-C₁–C₄-alkyl: C₁–C₄-alkoxy as mentioned above        and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,        3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,        2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,        2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,        1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,        2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,        1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,        1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and        1-ethyl-2-methylpropoxy;    -   C₁–C₄-haloalkoxy: a C₁–C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example fluoromethoxy,        difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,        bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,        2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,        3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,        2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,        2,3-difluoropropoxy, 2,3-dichloropropoxy,        3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,        1-(fluoromethyl)-2-fluoroethoxy,        1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,        4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and        nonafluorobutoxy;    -   C₁–C₆-haloalkoxy: C₁–C₄-haloalkoxy as mentioned above and also,        for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,        5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,        6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and        dodecafluorohexoxy;    -   C₁–C₄-alkylthio: for example methylthio, ethylthio, propylthio,        1-methylethylthio, butylthio, 1-methylpropylthio,        2-methylpropylthio and 1,1-dimethylethylthio;    -   C₁–C₆-alkylthio: C₁–C₄-alkylthio as mentioned above and, for        example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,        3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,        hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,        1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,        4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutylthio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;    -   C₁–C₄-haloalkylthio: a C₁–C₄-alkylthio radical as mentioned        above, which is partially or fully substituted by fluorine,        chlorine, bromine and/or iodine, i.e., for example        fluoromethylthio, difluoromethylthio, trifluoromethylthio,        chlorodifluoromethylthio, bromodifluoromethylthio,        2-fluorethylthio, 2-chloroethylthio, 2-bromoethylthio,        2-iodoethylthio, 2,2-difluoroethylthio,        2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,        2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,        2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,        2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,        3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,        2,2-difluoropropylthio, 2,3-difluoropropylthio,        2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,        3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,        heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,        1-(chloromethyl)-2-chloroethylthio,        1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,        4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;    -   C₁–C₆-haloalkylthio: C₁–C₄-haloalkylthio as mentioned above and        also, for example, 5-fluoropentylthio, 5-chloropentylthio,        5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio,        6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio,        6-iodohexylthio and dodecafluorohexylthio;    -   C₁–C₆-alkylsulfinyl (C₁–C₆-alkyl-S(═O)—): for example        methylsulfinyl, ethylsulfinyl, propylsulfinyl,        1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,        2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,        pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,        3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,        1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,        1,2-dimethylpropylsulfinyl, hexylsulfinyl,        1-methylpentylsulfinyl, 2-methylpentylsulfinyl,        3-methylpentylsulfinyl, 4-methylpentylsulfinyl,        1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,        1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,        2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,        1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,        1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,        1-ethyl-1-methylpropylsulfinyl and        1-ethyl-2-methylpropylsulfinyl;    -   C₁–C₆-haloalkylsulfinyl: a C₁–C₆-alkylsulfinyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e., for example        fluoromethylsulfinyl, difluoromethylsulfinyl,        trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,        bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,        2-chloroethylsulfinyl, 2-bromoethylsulfinyl,        2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,        2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,        2-chloro-2-fluoroethylsulfinyl,        2-chloro-2,2-difluoroethylsulfinyl,        2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,        2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,        2-chloropropylsulfinyl, 3-chloropropylsulfinyl,        2-bromopropylsulfinyl, 3-bromopropylsulfinyl,        2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,        2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,        3,3,3-trichloropropylsulfinyl,        2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,        1-(fluoromethyl)-2-fluoroethylsulfinyl,        1-(chloromethyl)-2-chloroethylsulfinyl,        1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,        4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,        nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,        5-chloropentylsulfinyl, 5-bromopentylsulfinyl,        5-iodopentylsulfinyl, undecafluoropentylsulfinyl,        6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,        6-bromohexylsulfinyl, 6-iodohexylsulfinyl and        dodecafluorohexylsulfinyl;    -   C₁–C₄-alkylsulfonyl (C₁–C₄-alkyl-S(═O)₂—): for example        methylsulfonyl, ethylsulfonyl, propylsulfonyl,        1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,        2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;    -   C₁–C₆-alkylsulfonyl: C₁–C₄-alkylsulfonyl as mentioned above, and        also for example pentylsulfonyl, 1-methylbutylsulfonyl,        2-methylbutylsulfonyl, 3-methylbutylsulfonyl,        1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,        2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl,        hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl,        3-methylpentylsulfonyl, 4-methylpentylsulfonyl,        1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,        1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,        2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,        1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,        1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,        1-ethyl-1-methylpropylsulfonyl and        1-ethyl-2-methylpropylsulfonyl;    -   C₁–C₄-haloalkylsulfonyl: a C₁–C₄-alkylsulfonyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e., for example        fluoromethylsulfonyl, difluoromethylsulfonyl,        trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,        bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,        2-chloroethylsulfonyl, 2-bromoethylsulfonyl,        2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,        2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,        2-chloro-2,2-difluoroethylsulfonyl,        2,2-dichloro-2-fluoroethylsulfonyl,        2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,        2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,        2-chloropropylsulfonyl, 3-chloropropylsulfonyl,        2-bromopropylsulfonyl, 3-bromopropylsulfonyl,        2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,        2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,        3,3,3-trichloropropylsulfonyl,        2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,        1-(fluoromethyl)-2-fluoroethylsulfonyl,        1-(chloromethyl)-2-chloroethylsulfonyl,        1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,        4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and        nonafluorobutylsulfonyl;    -   C₁–C₆-haloalkylsulfonyl: a C₁–C₄-haloalkylsulfonyl radical as        mentioned above, and also 5-fluoropentylsulfonyl,        5-chloropentylsulfonyl, 5-bromopentylsulfonyl,        5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,        6-bromohexylsulfonyl, 6-iodohexylsulfonyl and        dodecafluorohexylsulfonyl;    -   C₁–C₄-alkoxycarbonyl: for example methoxycarbonyl,        ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl,        butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl        and 1,1-dimethoxycarbonyl;    -   C₁–C₄-haloalkoxycarbonyl: a C₁–C₄-alkoxycarbonyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e., for example        fluoromethoxycarbonyl, difluoromethoxycarbonyl,        trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl,        bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl,        2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,        2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,        2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,        2-chloro-2,2-difluoroethoxycarbonyl,        2,2-dichloro-2-fluoroethoxycarbonyl,        2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl,        2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl,        2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl,        2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,        2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,        2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,        3,3,3-trichloropropoxycarbonyl,        2,2,3,3,3-pentafluoropropoxycarbonyl,        heptafluoropropoxycarbonyl,        1-(fluoromethyl)-2-fluoroethoxycarbonyl,        1-(chloromethyl)-2-chloroethoxycarbonyl,        1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,        4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl and        4-iodobutoxycarbonyl;    -   C₃–C₆-alkenyloxy: for example prop-1-en-1-yloxy,        prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy,        buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy,        2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy,        2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy,        penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy,        2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy,        1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy,        3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy,        2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy,        1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy,        1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy,        1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy,        hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy,        1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy,        3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,        1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,        3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,        1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,        3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,        1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,        3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,        1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,        1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,        1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy,        1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,        2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy,        2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,        3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,        1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,        1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy,        2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,        1,1,2-trimethylprop-2-en-1-yloxy,        1-ethyl-1-methylprop-2-en-1-yloxy,        1-ethyl-2-methylprop-1-en-1-yloxy and        1-ethyl-2-methylprop-2-en-1-yloxy;    -   C₃–C₆-alkynyloxy: for example prop-1-yn-1-yloxy,        prop-2-yn-1-yloxy, but-1-yn-1-yloxy, but-1-yn-3-yloxy,        but-1-yn-4-yloxy, but-2-yn-1-yloxy, pent-1-yn-1-yloxy,        pent-1-yn-3-yloxy, pent-1-yn-4-yloxy, pent-1-yn-5-yloxy,        pent-2-yn-1-yloxy, pent-2-yn-4-yloxy, pent-2-yn-5-yloxy,        3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy,        hex-1-yn-1-yloxy, hex-1-yn-3-yloxy, hex-1-yn-4-yloxy,        hex-1-yn-5-yloxy, hex-1-yn-6-yloxy, hex-2-yn-1-yloxy,        hex-2-yn-4-yloxy, hex-2-yn-5-yloxy, hex-2-yn-6-yloxy,        hex-3-yn-1-yloxy, hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy,        3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy,        3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy,        4-methylpent-2-yn-4-yloxy and 4-methylpent-2-yn-5-yloxy;    -   C₁–C₆-alkylamino: for example methylamino, ethylamino,        propylamino, 1-methylethylamino, butylamino,        1-methylpropylamino, 2-methylpropylamino,        1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,        2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,        1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,        1,2-dimethylpropylamino, 1-methylpentylamino,        2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,        1,1-dimethylbutylamino, 1,2-dimethylbutylamino,        1,3-dimethylbutylamino, 2,2-dimethylbutylamino,        2,3-dimethylbutylamino, 3,3-dimethylbutylamino,        1-ethylbutylamino, 2-ethylbutylamino,        1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,        1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;    -   di(C₁–C₄-alkyl)amino and the dialkylamino moieties of        di(C₁–C₄-alkyl)aminoimino-C₁–C₄-alkyl: for example        N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,        N,N-di(1-methylethyl)amino, N,N-dibutylamino,        N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,        N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,        N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,        N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,        N-methyl-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,        N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,        N-ethyl-N-(1-methylpropyl)amino,        N-ethyl-N-(2-methylpropyl)amino,        N-ethyl-N-(1,1-dimethylethyl)amino,        N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,        N-(1-methylpropyl)-N-propylamino,        N-(2-methylpropyl)-N-propylamino,        N-(1,1-dimethylethyl)-N-propylamino,        N-butyl-N-(1-methylethyl)amino,        N-(1-methylethyl)-N-(1-methylpropyl)amino,        N-(1-methylethyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,        N-butyl-N-(1-methylpropyl)amino,        N-butyl-N-(2-methylpropyl)amino,        N-butyl-N-(1,1-dimethylethyl)amino,        N-(1-methylpropyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and        N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;    -   di(C₁–C₆-alkyl)amino: di(C₁–C₄-alkyl)amino as mentioned above,        and also N,N-dipentylamino, N,N-dihexylamino,        N-methyl-N-pentylamino, N-ethyl-N-pentylamino,        N-methyl-N-hexylamino or N-ethyl-N-hexylamino;    -   di(C₁–C₄-alkyl)amino-C₁–C₄-alkyl: C₁–C₄-alkyl which is        substituted by di(C₁–C₄-alkyl)amino as mentioned above, i.e.,        for example N,N-dimethylaminomethyl, N,N-diethylaminomethyl,        N,N-dipropylaminomethyl, N,N-di(1-methylethyl)aminomethyl,        N,N-dibutylaminomethyl, N,N-di(1-methylpropyl)aminomethyl,        N,N-di(2-methylpropyl)aminomethyl,        N,N-di(1,1-dimethylethyl)aminomethyl,        N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl,        N-methyl-N-(1-methylethyl)aminomethyl,        N-butyl-N-methylaminomethyl,        N-methyl-N-(1-methylpropyl)aminomethyl,        N-methyl-N-(2-methylpropyl)aminomethyl,        N-(1,1-dimethylethyl)-N-methylaminomethyl,        N-ethyl-N-propylaminomethyl,        N-ethyl-N-(1-methylethyl)aminomethyl,        N-butyl-N-ethylaminomethyl,        N-ethyl-N-(1-methylpropyl)aminomethyl,        N-ethyl-N-(2-methylpropyl)aminomethyl,        N-ethyl-N-(1,1-dimethylethyl)aminomethyl,        N-(1-methylethyl)-N-propylaminomethyl,        N-butyl-N-propylaminomethyl,        N-(1-methylpropyl)-N-propylaminomethyl,        N-(2-methylpropyl)-N-propylaminomethyl,        N-(1,1-dimethylethyl)-N-propylaminomethyl,        N-butyl-N-(1-methylethyl)aminomethyl,        N-(1-methylethyl)-N-(1-methylpropyl)aminomethyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminomethyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminomethyl,        N-butyl-N-(1-methylpropyl)aminomethyl,        N-butyl-N-(2-methylpropyl)aminomethyl,        N-butyl-N-(1,1-dimethylethyl)aminomethyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminomethyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminomethyl,        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminomethyl,        2-(N,N-dimethylamino)ethyl, 2-(N,N-diethylamino)ethyl,        2-(N,N-dipropylamino)ethyl, 2-[N,N-di(1-methylethyl)amino]ethyl,        2-[N,N-dibutylamino]ethyl, 2-[N,N-di(1-methylpropyl)amino]ethyl,        2-[N,N-di(2-methylpropyl)amino]ethyl,        2-[N,N-di(1,1-dimethylethyl)amino]ethyl,        2-[N-ethyl-N-methylamino]ethyl, 2-[N-methyl-N-propylamino]ethyl,        2-[N-methyl-N-(1-methylethyl)amino]ethyl,        2-[N-butyl-N-methylamino]ethyl,        2-[N-methyl-N-(1-methylpropyl)amino]ethyl,        2-[N-methyl-N-(2-methylpropyl)amino]ethyl,        2-[N-(1,1-dimethylethyl)-N-methylamino]ethyl,        2-[N-ethyl-N-propylamino]ethyl,        2-[N-ethyl-N-(1-methylethyl)amino]ethyl,        2-[N-butyl-N-ethylamino]ethyl,        2-[N-ethyl-N-(1-methylpropyl)amino]ethyl,        2-[N-ethyl-N-(2-methylpropyl)amino]ethyl,        2-[N-ethyl-N-(1,1-dimethylethylamino]ethyl,        2-[N-(1-methylethyl)-N-propylamino]ethyl,        2-[N-butyl-N-propylamino]ethyl,        2-[N-(1-methylpropyl)-N-propylamino]ethyl,        2-[N-(2-methylpropyl)-N-propylamino]ethyl,        2-[N-(1,1-dimethylethyl)-N-propylamino]ethyl,        2-[N-butyl-N-(1-methylethyl)amino]ethyl,        2-[N-(1-methylethyl)-N-(1-methylpropyl)amino]ethyl,        2-[N-(1-methylethyl)-N-(2-methylpropyl)amino]ethyl,        2-[N-(1,1-dimethylethyl)-N-(1-methylethyl)amino]ethyl,        2-[N-butyl-N-(1-methylpropyl)amino]ethyl,        2-[N-butyl-N-(2-methylpropyl)amino]ethyl,        2-[N-butyl-N-(1,1-dimethylethyl)amino]ethyl,        2-[N-(1-methylpropyl)-N-(2-methylpropyl)amino]ethyl,        2-[N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino]ethyl,        2-[N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino]ethyl,        3-(N,N-dimethylamino)propyl, 3-(N,N-diethylamino)propyl,        4-(N,N-dimethylamino)butyl and 4-(N,N-diethylamino)butyl;    -   C₁–C₄-alkoxy-C₁–C₄-alkyl: C₁–C₄-alkyl which is substituted by        C₁–C₄-alkoxy as mentioned above, i.e., for example        methoxymethyl, ethoxymethyl, propoxymethyl,        (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,        (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,        2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,        2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,        2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,        2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,        2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,        2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,        2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,        3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,        3-(1-methylethoxy)propyl, 3-(butoxy)propyl,        3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,        3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,        2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,        2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,        2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,        3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,        3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,        3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,        4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,        4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and        4-(1,1-dimethylethoxy)butyl;    -   C₁–C₄-alkylthio-C₁–C₄-alkyl: C₁–C₄-alkyl which is substituted by        C₁–C₄-alkylthio as mentioned above, i.e., for example        methylthiomethyl, ethylthiomethyl, propylthiomethyl,        (1-methylethylthio)methyl, butylthiomethyl,        (1-methylpropylthio)methyl, (2-methylpropylthio)methyl,        (1,1-dimethylethylthio)methyl, 2-methylthioethyl,        2-ethylthioethyl, 2-(propylthio)ethyl,        2-(1-methylethylthio)ethyl, 2-(butylthio)ethyl,        2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl,        2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl,        3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl,        3-(propylthio)propyl, 3-(butylthio)propyl, 4-(methylthio)butyl,        4-(ethylthio)butyl, 4-(propylthio)butyl and 4-(butylthio)butyl;    -   C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl: C₁–C₄-alkyl which is        substituted by C₁–C₄-alkoxycarbonyl as mentioned above, i.e.,        for example methoxycarbonylmethyl, ethoxycarbonylmethyl,        propoxycarbonylmethyl, (1-methylethoxycarbonyl)methyl,        butoxycarbonylmethyl, (1-methylpropoxycarbonyl)methyl,        (2-methylpropoxycarbonyl)methyl,        (1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl,        2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,        2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl,        2-(1-methylpropoxycarbonyl)ethyl,        2-(2-methylpropoxycarbonyl)ethyl,        2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl,        2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl,        2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl,        2-(1-methylpropoxycarbonyl)propyl,        2-(2-methylpropoxycarbonyl)propyl,        2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl,        3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl,        3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl,        3-(1-methylpropoxycarbonyl)propyl,        3-(2-methylpropoxycarbonyl)propyl,        3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl,        2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl,        2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl,        2-(1-methylpropoxycarbonyl)butyl,        2-(2-methylpropoxycarbonyl)butyl,        2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl,        3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl,        3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl,        3-(1-methylpropoxycarbonyl)butyl,        3-(2-methylpropoxycarbonyl)butyl,        3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl,        4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl,        4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl,        4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and        4-(1,1-dimethylethoxycarbonyl)butyl;    -   C₁–C₄-alkoxy-C₂–C₄-alkoxy: C₂–C₄-alkoxy which is substituted by        C₁–C₄-alkoxy as mentioned above, i.e., for example        2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy,        2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy,        2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,        2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy,        2-(ethoxy)propoxy, 2-(propoxy)propoxy,        2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,        2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,        2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy,        3-(ethoxy)propoxy, 3-(propoxy)propoxy,        3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,        3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,        3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,        2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy,        2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy,        2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy,        3-(methoxy)butoxy, 3-(ethoxy)-butoxy, 3-(propoxy)butoxy,        3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,        3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,        3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy,        4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy,        4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy,        4-(2-methylpropoxy)butoxy and 4-(1,1-dimethylethoxy)butoxy;    -   C₂–C₆-alkanediyl: for example ethane-1,2-diyl, propane-1,3-diyl,        butane-1,4-diyl, pentane-1,5-diyl and hexane-1,6-diyl;    -   C₃–C₆-cycloalkyl: for example cyclopropyl, cyclobutyl,        cyclopentyl or cyclohexyl;    -   C₃–C₈-cycloalkyl: C₃–C₆-cycloalkyl as mentioned above, and also        cycloheptyl and cyclooctyl.

All phenyl rings are preferably unsubstituted or have attached to themone to three halogen atoms and/or a nitro group, a cyano radical and/orone or two methyl, trifluoromethyl, methoxy or trifluoromethoxysubstituents.

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, in each case alone or in combination:

-   R¹, R² are nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl; particularly    preferably nitro, halogen, such as, for example, chlorine and    bromine, C₁–C₆-alkyl, such as, for example, methyl and ethyl,    C₁–C₆-alkoxy, such as, for example, methoxy and ethoxy,    C₁–C₆-haloalkyl, such as, for example, difluoromethyl and    trifluoromethyl, C₁–C₆-alkylthio, such as, for example, methylthio    and ethylthio, C₁–C₆-alkylsulfinyl, such as, for example,    methylsulfinyl and ethylsulfinyl, C₁–C₆-alkylsulfonyl, such as, for    example, methylsulfonyl, ethylsulfonyl and propylsulfonyl, or    C₁–C₆-haloalkylsulfonyl, such as, for example,    trifluoromethylsulfonyl and pentafluoroethylsulfonyl;-   R³ is hydrogen;-   R⁴ is hydrogen;-   R⁵, R⁶ are hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,    C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,    C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,    C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,    di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the two    last-mentioned substituents may be partially or fully halogenated    and/or may carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;        or-   R⁵ and R⁶ together form a C₂–C₆-alkanediyl chain which may be mono-    to tetrasubstituted by C₁–C₄-alkyl and/or may be interrupted by    oxygen or an unsubstituted or C₁–C₄-alkyl-substituted nitrogen;    -   R⁵ is particularly preferably hydrogen, halogen, cyano, nitro,        C₁–C₄-alkyl, C₁–C₄-alkoxy-C₁–C₄-alkyl,        C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl, C₁–C₄-alkylthio-C₁–C₄-alkyl,        C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl, C₃–C₈-cycloalkyl,        C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy, C₁–C₄-haloalkoxy,        C₁–C₄-alkylthio, C₁–C₄-haloalkylthio, di(C₁–C₄-alkyl)amino,        COR⁸, phenyl or benzyl, where the two last-mentioned        substituents may be partially or fully halogenated and/or may        carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   R⁶ is particularly preferably hydrogen or C₁–C₄-alkyl;    -   very particularly preferably, R⁵ is hydrogen, C₁–C₄-alkyl,        C₁–C₄-haloalkyl, C₁–C₄-alkoxycarbonyl or CONR⁹R¹⁰;    -   very particularly preferably, R⁶ is hydrogen or C₁–C₄-alkyl;    -   most preferably, R⁵ is hydrogen or C₁–C₄-alkyl, in particular        hydrogen;    -   most preferably, R⁶ is hydrogen;-   R⁷ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-alkylsulfonyl, amino,    C₁–C₆-alkylamino, di(C₁–C₆-alkyl)amino, di(C₁–C₄-alkoxy)methyl or    COR⁸;    -   particularly preferably C₁–C₄-alkyl, such as, for example,        methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,        hydroxycarbonyl or C₁–C₄-alkoxycarbonyl, such as, for example,        methoxycarbonyl or ethoxycarbonyl;-   R⁸ is C₁–C₄-alkyl, hydroxyl, C₁–C₄-alkoxy or NR⁹R¹⁰;-   R⁹ is hydrogen or C₁–C₄-alkyl;-   R¹⁰ is C₁–C₄-alkyl;-   R¹² is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkylcarbonyl,    C₁–C₄-haloalkylcarbonyl, C₁–C₄-alkylsulfonyl,    C₁–C₄-haloalkylsulfonyl, phenyl, benzyl, phenylcarbonyl or    phenylcarbonyl [sic] or phenylsulfonyl, where the phenyl radical of    the five last-mentioned substituents may be partially or fully    halogenated and/or may carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   is particularly preferably hydrogen, C₁–C₄-alkyl,        C₁–C₄-alkylsulfonyl, C₁–C₄-haloalkylsulfonyl, phenyl, benzyl or        phenylsulfonyl, where the phenyl radical of the three        last-mentioned substituents may be partially or fully        halogenated and/or may carry one to three of the following        groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   is very particularly preferably hydrogen or C₁–C₄-alkylsulfonyl,        C₁–C₄-haloalkylsulfonyl or phenylsulfonyl, where the phenyl        radical may be partially or fully halogenated and/or may carry        one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;    -   is likewise particularly preferably hydrogen, C₁–C₄-alkyl,        C₁–C₄-alkylsulfonyl, C₁–C₄-haloalkylsulfonyl, thienylmethyl,        phenyl, benzyl, phenylsulfonyl or phenylcarbonylmethyl, where        the phenyl radical of the four last-mentioned substituents may        be partially or fully halogenated and/or may carry one to three        of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;-   R¹³ is C₁–C₆-alkyl or C₃–C₆-cycloalkyl;    -   particularly preferably methyl, ethyl, 1-methylethyl,        1,1-dimethylethyl or cyclopropyl;-   R¹⁴ is hydrogen or C₁–C₆-alkyl;    -   particularly preferably hydrogen or methyl.

The following embodiments of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I are to beemphasized:

1. In a preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R¹ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy        or C₁–C₆-haloalkoxy;        -   particularly preferably nitrogen, halogen, such as chlorine            or bromine, C₁–C₄-alkyl, such as methyl or ethyl,            C₁–C₄-haloalkyl, such as difluoromethyl or trifluoromethyl,            C₁–C₄-alkoxy, such as methoxy or ethoxy, or C₁–C₄-haloalkoxy            such as difluoromethoxy or trifluoromethoxy;        -   particularly preferably halogen, such as chlorine or            bromine, C₁–C₄-alkyl, such as methyl or ethyl or            C₁–C₄-alkoxy, such as methoxy or ethoxy;        -   most preferably halogen, such as chlorine or bromine,            C₁–C₄-alkyl, such as methyl or ethyl;    -   R² is halogen, C₁–C₆-haloalkyl, C₁–C₆-alkylthio,        C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,        C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl or        C₁–C₆-haloalkylsulfonyl;        -   particularly preferably halogen, such as fluorine or            chlorine, C₁–C₄-haloalkyl, such as difluoromethyl or            trifluoromethyl, or C₁–C₄-alkylsulfonyl, such as            methylsulfonyl or ethylsulfonyl;        -   very particularly preferably halogen, such as fluorine or            chlorine, or C₁–C₄-alkylsulfonyl, such as methylsulfonyl or            ethylsulfonyl.

2. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R³ is hydrogen.

3. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R³ is halogen or C₁–C₄-alkyl;        -   particularly preferably chlorine or methyl.

4. In a further [lacuna] embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R⁴ is hydrogen;    -   R⁵ is hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,        C₁–C₄-alkoxy-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,        C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,        C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,        C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,        di(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,        CONR⁹R¹⁰, phenyl or benzyl, where the two last-mentioned        substituents may be partially or fully halogenated and/or may        carry one to three of the following groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;        -   is particularly preferably hydrogen, C₁–C₄-alkyl,            C₁–C₄-haloalkyl, C₁–C₄-alkoxycarbonyl or CONR⁹R¹⁰;        -   very particularly preferably hydrogen or C₁–C₄-alkyl, such            as methyl or ethyl;        -   most preferably hydrogen;    -   R⁶ is hydrogen or C₁–C₄-alkyl, such as methyl or ethyl;        -   particularly preferably hydrogen.

5. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R⁷ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,        C₁–C₆-alkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-alkylsulfonyl,        amino, C₁–C₆-alkylamino, di(C₁–C₆-alkyl)amino,        di(C₁–C₆-alkoxy)methyl, formyl, C₁–C₄-alkylcarbonyl,        C₁–C₄-haloalkylcarbonyl, hydroxycarbonyl, C₁–C₄-alkoxycarbonyl,        C₁–C₄-haloalkoxycarbonyl or CONR⁹R¹⁰;        -   particularly preferably halogen, such as chlorine or            bromine, C₁–C₄-alkyl, such as methyl, ethyl, 1-methylethyl            or 1,1-dimethylethyl, C₁–C₄-alkoxy, such as methoxy or            ethoxy, C₁–C₄-alkylthio, such as methylthio or ethylthio,            C₁–C₄-alkylsulfinyl, such as methylsulfinyl or            ethylsulfinyl, C₁–C₄-alkylsulfonyl, such as methylsulfonyl            or ethylsulfonyl, amino, C₁–C₄-alkylamino, such as            methylamino or ethylamino, di(C₁–C₄-alkyl)amino, such as            dimethylamino or diethylamino, di(C₁–C₄-alkoxy)methyl, such            as dimethoxymethyl or diethoxymethyl, C₁–C₄-alkylcarbonyl,            such as methylcarbonyl or ethylcarbonyl, hydroxycarbonyl,            C₁–C₄-alkoxycarbonyl, such as methoxycarbonyl or            ethoxycarbonyl, or CONR⁹R¹⁰;        -   very particularly preferably C₁–C₄-alkyl, such as methyl,            ethyl, 1-methylethyl or 1,1-dimethylethyl, hydroxycarbonyl            or C₁–C₄-alkoxycarbonyl, such as methoxycarbonyl or            ethoxycarbonyl;        -   most preferably C₁–C₄-alkyl, such as methyl, ethyl,            1-methylethyl or 1,1-dimethylethyl;

6. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R¹² is C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkylcarbonyl,        C₁–C₄-haloalkylcarbonyl, C₁–C₄-alkylsulfonyl,        C₁–C₄-haloalkylsulfonyl, phenyl, benzyl, phenylcarbonyl or        phenylsulfonyl, where the phenyl radical of the four        last-mentioned substituents may be partially or fully        halogenated and/or may carry one to three of the following        groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;        -   is particularly preferably C₁–C₄-alkyl, C₁–C₄-alkylsulfonyl,            C₁–C₄-haloalkylsulfonyl, phenyl, benzyl or phenylsulfonyl,            where the phenyl radical of the three last-mentioned            substituents may be partially or fully halogenated and/or            may carry one to three of the following groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;        -   is very particularly preferably C₁–C₄-alkylsulfonyl,            C₁–C₄-haloalkylsulfonyl or phenylsulfonyl, where the phenyl            radical may be partially or fully halogenated and/or may            carry one to three of the following groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;        -   is likewise particularly preferably benzyl, where the phenyl            radical may be partially or fully halogenated and/or may            carry one to three of the following groups: nitro, cyano,            C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy.

7. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R¹² is C₁–C₄-alkyl, C₃–C₄-alkynyl, thienylmethyl, benzyl,        phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, where        the phenyl radical of the four last-mentioned substituents may        be partially or fully halogenated and/or may carry one to three        of the following groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;        -   is particularly preferably thienylmethyl, such as            3-thienylmethyl, benzyl, phenylcarbonyl, phenylsulfonyl or            phenylcarbonylmethyl, where the phenyl radical of the four            last-mentioned substituents may be partially or fully            halogenated and/or may carry one to three of the following            groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy.

8. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I, R¹² ishydroxyl.

9. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R¹³ is C₁–C₄-alkyl, such as methyl, ethyl, methylethyl or        1,1-dimethylethyl, or C₃–C₆-cycloalkyl, such as cyclopropyl;        -   particularly preferably C₁–C₄-alkyl, such as methyl, ethyl,            1-methylethyl or 1,1-dimethylethyl;        -   likewise preferably C₃–C₆-cycloalkyl, such as cyclopropyl;    -   R¹⁴ is hydrogen or C₁–C₄-alkyl, such as, for example, methyl or        ethyl;        -   particularly preferably hydrogen or methyl.

10. In a further preferred embodiment of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,

-   -   R¹ is halogen C₁–C₄-alkyl or C₁–C₄-alkoxy;    -   R² is halogen or C₁–C₄-alkylsulfonyl;    -   R³, R⁴ and R⁶ are hydrogen;    -   R⁵ is hydrogen or C₁–C₄-alkyl; in particular hydrogen    -   R⁷ is C₁–C₄-alkyl, di(C₁–C₄-alkoxy)methyl, hydroxycarbonyl or        C₁–C₄-alkoxycarbonyl;    -   R¹² is hydrogen, C₃–C₄-alkynyl, thienylmethyl, benzyl,        phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, where        the phenyl radical of the four last-mentioned substituents may        be partially or fully halogenated and/or may carry one to three        of the following groups:        -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or            C₁–C₄-haloalkoxy;    -   R¹³ is C₁–C₄-alkyl, C₁–C₄-haloalkyl or cyclopropyl;        -   in particular C₁–C₄-alkyl or cyclopropyl;    -   R¹⁴ is hydrogen, C₁–C₄-alkyl or cyclopropyl;        -   in particular hydrogen or C₁–C₄-alkyl.

Most particular preference is given to the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula Ia1 (≡Iwhere R¹═Cl; R²═SO₂CH₃; R³, R⁴, R¹², R¹⁴═H; R¹³═CH₃), in particular tothe compounds Ia1.1 to Ia1.64, where the radical definitions R¹ to R¹⁴are of particular importance for the compounds according to theinvention, not only in combination with one another but in each casealso on their own.

TABLE 1 No. R⁵ R⁶ R⁷ Ial.1 H H CH₃ Ial.2 Cl H CH₃ Ial.3 Br H CH₃ Ial.4CN H CH₃ Ial.5 NO₂ H CH₃ Ial.6 CH₃ H CH₃ Ial.7 CH₂CH₃ H CH₃ Ial.8CH(CH₃)₂ H CH₃ Ial.9 C(CH₃)3 H CH₃ Ial.10 CHO H CH₃ Ial.11 CH═NOH H CH₃Ial.12 CH═NOCH₃ H CH₃ Ial.13 CH═NOCH₂CH₃ H CH₃ Ial.14 COCH₃ H CH₃ Ial.15C(═NOH)CH₃ H CH₃ Ial.16 C(═NOCH₃)CH₃ H CH₃ Ial.17 C(═NOCH₂CH₃)CH₃ H CH₃Ial.18 CH═NN(CH₃)₂ H CH₃ Ial.19 C[═NN(CH₃)₂]CH₃ H CH₃ Ial.20 COOH H CH₃Ial.21 COOCH₃ H CH₃ Ial.22 COOCH₂CH₃ H CH₃ Ial.23 OCH₃ H CH₃ Ial.24OCH₂CH₃ H CH₃ Ial.25 SCH₃ H CH₃ Ial.26 CH₂F H CH₃ Ial.27 CHF₂ H CH₃Ial.28 CF₃ H CH₃ Ial.29 CF₂CF₃ H CH₃ Ial.30 CH₂Cl H CH₃ Ial.31 CH₂CN HCH₃ Ial.32 CH₂—CH₂ CH₃ Ial.33 CH₂—CH₂—CH₂ CH₃ Ial.34 CH₂—CH₂—CH₂—CH₂ CH₃Ial.35 CH₂—CH₂—CH₂—CH₂—CH₂ CH₃ Ial.36 CH₃ CH₃ CH₃ Ial.37 CH₃ CH₂CH₃ CH₃Ial.38 CF₃ COCH₃ CH₃ Ial.39 CF₃ COOCH₃ CH₃ Ial.40 CN COCH₃ CH₃ Ial.41 CNCOOCH₃ CH₃ Ial.42 CN CN CH₃ Ial.43 COCH₃ COCH₃ CH₃ Ial.44 COCH₃ COOCH₃CH₃ Ial.45 H H CH₂CH₃ Ial.46 H H CH(CH₃)₂ Ial.47 H H C(CH₃)₃ Ial.48 H HCl Ial.49 H H OCH₃ Ial.50 H H SCH₃ Ial.51 H H SOCH₃ Ial.52 H H SO₂CH₃Ial.53 H H CN Ial.54 H H CHO Ial.55 H H CH═NOH Ial.56 H H CH═NOCH₃Ial.57 H H CH═NOCH₂CH₃ Ial.58 H H COCH₃ Ial.59 H H C(═NOH)CH₃ Ial.60 H HC(═NOCH₃)CH₃ Ial.61 H H COOH Ial.62 H H COOCH₃ Ial.63 H H COOCH₂CH₃Ial.64 H H CH(OCH₂CH₃)₂

Particular preference is likewise given to the compounds Ia2, inparticular to the compounds Ia2.1–Ia2.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia3, inparticular to the compounds Ia3.1–Ia3.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia4, inparticular to the compounds Ia4.1–Ia4.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia5, inparticular to the compounds Ia5.1–Ia5.64 which differ from compoundsIa1.1–Ia1.64 in that R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia6, inparticular to the compounds Ia6.1–Ia6.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia7, inparticular to the compounds Ia7.1–Ia7.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia8, inparticular to the compounds Ia8.1–Ia8.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is tert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia9, inparticular to the compounds Ia9.1–Ia9.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl.

Particular preference is likewise given to the compounds Ia10, inparticular to the compounds Ia10.1–Ia10.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia11, inparticular to the compounds Ia11.1–Ia11.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia12, inparticular to the compounds Ia12.1–Ia12.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia13, inparticular to the compounds Ia13.1–Ia13.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl.

Particular preference is likewise given to the compounds Ia14, inparticular to the compounds Ia14.1–Ia14.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia15, inparticular to the compounds Ia15.1–Ia15.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia16, inparticular to the compounds Ia16.1–Ia16.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia17, inparticular to the compounds Ia17.1–Ia17.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl.

Particular preference is likewise given to the compounds Ia18, inparticular to the compounds Ia18.1–Ia18.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia19, inparticular to the compounds Ia19.1–Ia19.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia20, inparticular to the compounds Ia20.1–Ia20.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia21, inparticular to the compounds Ia21.1–Ia21.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia22, inparticular to the compounds Ia22.1–Ia22.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia23, inparticular to the compounds Ia23.1–Ia23.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia24, inparticular to the compounds Ia24.1–Ia24.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia25, inparticular to the compounds Ia25.1–Ia25.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy.

Particular preference is likewise given to the compounds Ia26, inparticular to the compounds Ia26.1–Ia26.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia27, inparticular to the compounds Ia27.1–Ia27.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia28, inparticular to the compounds Ia28.1–Ia28.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia29, inparticular to the compounds Ia29.1–Ia29.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia30, inparticular to the compounds Ia30.1–Ia30.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R¹³ is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia31, inparticular to the compounds Ia31.1–Ia31.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia32, inparticular to the compounds Ia32.1–Ia32.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R¹³ is tert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia33, inparticular to the compounds Ia33.1–Ia33.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia34, inparticular to the compounds Ia34.1–Ia34.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia35, inparticular to the compounds Ia35.1–Ia35.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia36, inparticular to the compounds Ia36.1–Ia36.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia37, inparticular to the compounds Ia37.1–Ia37.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹⁴ is ethyl.

Particular preference is likewise given to the compounds Ia38, inparticular to the compounds Ia38.1–Ia38.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia39, inparticular to the compounds Ia39.1–Ia39.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia40, inparticular to the compounds Ia40.1–Ia40.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia41, inparticular to the compounds Ia41.1–Ia41.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia42, inparticular to the compounds Ia42.1–Ia42.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia43, inparticular to the compounds Ia43.1–Ia43.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia44, inparticular to the compounds Ia44.1–Ia44.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia45, inparticular to the compounds Ia45.1–Ia45.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia46, inparticular to the compounds Ia46.1–Ia46.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia47, inparticular to the compounds Ia47.1–Ia47.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia48, inparticular to the compounds Ia48.1–Ia48.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia49, inparticular to the compounds Ia49.1–Ia49.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia50, inparticular to the compounds Ia50.1–Ia50.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia51, inparticular to the compounds Ia51.1–Ia51.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia52, inparticular to the compounds Ia52.1–Ia52.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia53, inparticular to the compounds Ia53.1–Ia53.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia54, inparticular to the compounds Ia54.1–Ia54.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl, R¹³ isethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia55, inparticular to the compounds Ia55.1–Ia55.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia56, inparticular to the compounds Ia56.1–Ia56.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is ethylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia57, inparticular to the compounds Ia57.1–Ia57.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia58, inparticular to the compounds Ia58.1–Ia58.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia59, inparticular to the compounds Ia59.1–Ia59.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia60, inparticular to the compounds Ia60.1–Ia60.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia61, inparticular to the compounds Ia61.1–Ia61.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia62, inparticular to the compounds Ia62.1–Ia62.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia63, inparticular to the compounds Ia63.1–Ia63.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia64, inparticular to the compounds Ia64.1–Ia64.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia65, inparticular to the compounds Ia65.1–Ia65.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine.

Particular preference is likewise given to the compounds Ia66, inparticular to the compounds Ia66.1–Ia66.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia67, inparticular to the compounds Ia67.1–Ia67.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia68, inparticular to the compounds Ia68.1–Ia68.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia69, inparticular to the compounds Ia69.1–Ia69.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia70, inparticular to the compounds Ia70.1–Ia70.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹³ is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia71, inparticular to the compounds Ia71.1–Ia71.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia72, inparticular to the compounds Ia72.1–Ia72.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia73, inparticular to the compounds Ia73.1–Ia73.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R² is chlorine.

Particular preference is likewise given to the compounds Ia74, inparticular to the compounds Ia74.1–Ia74.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia75, inparticular to the compounds Ia75.1–Ia75.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia76, inparticular to the compounds Ia76.1–Ia76.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia77, inparticular to the compounds Ia77.1–Ia77.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R² is chlorine.

Particular preference is likewise given to the compounds Ia78, inparticular to the compounds Ia78.1–Ia78.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia79, inparticular to the compounds Ia79.1–Ia79.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia80, inparticular to the compounds Ia80.1–Ia80.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia81, inparticular to the compounds Ia81.1–Ia81.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl and R² is chlorine.

Particular preference is likewise given to the compounds Ia82, inparticular to the compounds Ia82.1–Ia82.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia83, inparticular to the compounds Ia83.1–Ia83.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia84, inparticular to the compounds Ia84.1–Ia84.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia85, inparticular to the compounds Ia85.1–Ia85.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia86, inparticular to the compounds Ia86.1–Ia86.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia87, inparticular to the compounds Ia87.1–Ia87.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia88, inparticular to the compounds Ia88.1–Ia88.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia89, inparticular to the compounds Ia89.1–Ia89.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R² is chlorine.

Particular preference is likewise given to the compounds Ia90, inparticular to the compounds Ia90.1–Ia90.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia91, inparticular to the compounds Ia91.1–Ia91.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia92, inparticular to the compounds Ia92.1–Ia92.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia93, inparticular to the compounds Ia93.1–Ia93.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia94, inparticular to the compounds Ia94.1–Ia94.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine, R¹³ is ethyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia95, inparticular to the compounds Ia95.1–Ia95.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine, R¹³ is isopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia96, inparticular to the compounds Ia96.1–Ia96.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine, R¹³ is tert-butyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia97, inparticular to the compounds Ia97.1–Ia97.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl.

Particular preference is likewise given to the compounds Ia98, inparticular to the compounds Ia98.1–Ia98.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia99, inparticular to the compounds Ia99.1–Ia99.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia100, inparticular to the compounds Ia100.1–Ia100.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia101, inparticular to the compounds Ia101.1–Ia101.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia102, inparticular to the compounds Ia102.1–Ia102.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia103, inparticular to the compounds Ia103.1–Ia103.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia104, inparticular to the compounds Ia104.1–Ia104.64 which differ from compoundsIa1.1–Ia1.64 in that R² is trifluoromethyl, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia105, inparticular to the compounds Ia105.1–Ia105.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R² is trifluoromethyl.

Particular preference is likewise given to the compounds Ia106, inparticular to the compounds Ia106.1–Ia106.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is trifluoromethyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia107, inparticular to the compounds Ia107.1–Ia107.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is trifluoromethyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia108, inparticular to the compounds Ia108.1–Ia108.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is trifluoromethyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia109, inparticular to the compounds Ia109.1–Ia109.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R² is trifluoromethyl.

Particular preference is likewise given to the compounds Ia110, inparticular to the compounds Ia110.1–Ia110.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is trifluoromethyl andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia111, inparticular to the compounds Ia111.1–Ia111.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is trifluoromethyl andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia112, inparticular to the compounds Ia112.1–Ia112.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is trifluoromethyl andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia113, inparticular to the compounds Ia113.1–Ia113.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl.

Particular preference is likewise given to the compounds Ia114, inparticular to the compounds Ia114.1–Ia114.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia115, inparticular to the compounds Ia115.1–Ia115.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia116, inparticular to the compounds Ia116.1–Ia116.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia117, inparticular to the compounds Ia117.1–Ia117.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia118, inparticular to the compounds Ia118.1–Ia118.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl, R¹³ is ethyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia119, inparticular to the compounds Ia119.1–Ia119.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl, R¹³ is isopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia120, inparticular to the compounds Ia120.1–Ia120.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R² are trifluoromethyl, R¹³ is tert-butyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia121, inparticular to the compounds Ia121.1–Ia121.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy and R² is trifluoromethyl.

Particular preference is likewise given to the compounds Ia122, inparticular to the compounds Ia122.1–Ia122.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia123, inparticular to the compounds Ia123.1–Ia123.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia124, inparticular to the compounds Ia124.1–Ia124.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia125, inparticular to the compounds Ia125.1–Ia125.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia126, inparticular to the compounds Ia126.1–Ia126.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia127, inparticular to the compounds Ia127.1–Ia127.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia128, inparticular to the compounds Ia128.1–Ia128.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia129, inparticular to the compounds Ia129.1–Ia129.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine.

Particular preference is likewise given to the compounds Ia130, inparticular to the compounds Ia130.1–Ia130.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia131, inparticular to the compounds Ia131.1–Ia131.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia132, inparticular to the compounds Ia132.1–Ia132.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia133, inparticular to the compounds Ia133.1–Ia133.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia134, inparticular to the compounds Ia134.1–Ia134.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine, R¹³ is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia135, inparticular to the compounds Ia135.1–Ia135.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine, R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia136, inparticular to the compounds Ia136.1–Ia136.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is chlorine, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia137, inparticular to the compounds Ia137.1–Ia137.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R³ is chlorine.

Particular preference is likewise given to the compounds Ia138, inparticular to the compounds Ia138.1–Ia138.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R³ is chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia139, inparticular to the compounds Ia139.1–Ia139.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R³ is chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia140, inparticular to the compounds Ia140.1–Ia140.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R³ is chlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia141, inparticular to the compounds Ia141.1–Ia141.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R³ is chlorine.

Particular preference is likewise given to the compounds Ia142, inparticular to the compounds Ia142.1–Ia142.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R³ is chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia143, inparticular to the compounds Ia143.1–Ia143.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R³ is chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia144, inparticular to the compounds Ia144.1–Ia144.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R³ is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia145, inparticular to the compounds Ia145.1–Ia145.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R³ is chlorine.

Particular preference is likewise given to the compounds Ia146, inparticular to the compounds Ia146.1–Ia146.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia147, inparticular to the compounds Ia147.1–Ia147.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia148, inparticular to the compounds Ia148.1–Ia148.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia149, inparticular to the compounds Ia149.1–Ia149.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia150, inparticular to the compounds Ia150.1–Ia150.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia151, inparticular to the compounds Ia151.1–Ia151.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia152, inparticular to the compounds Ia152.1–Ia152.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia153, inparticular to the compounds Ia153.1–Ia153.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R² is ethylsulfonyl and R³ ischlorine.

Particular preference is likewise given to the compounds Ia154, inparticular to the compounds Ia154.1–Ia154.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl R² is ethylsulfonyl, R³ is chlorineand R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia155, inparticular to the compounds Ia155.1–Ia155.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R³ is chlorineand R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia156, inparticular to the compounds Ia156.1–Ia156.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R³ is chlorineand R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia157, inparticular to the compounds Ia157.1–Ia157.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R³is chlorine.

Particular preference is likewise given to the compounds Ia158, inparticular to the compounds Ia158.1–Ia158.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R³ ischlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia159, inparticular to the compounds Ia159.1–Ia159.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R³ ischlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia160, inparticular to the compounds Ia160.1–Ia160.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R³ ischlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia161, inparticular to the compounds Ia161.1–Ia161.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine.

Particular preference is likewise given to the compounds Ia162, inparticular to the compounds Ia162.1–Ia162.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia163, inparticular to the compounds Ia163.1–Ia163.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia164, inparticular to the compounds Ia164.1–Ia164.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia165, inparticular to the compounds Ia165.1–Ia165.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia166, inparticular to the compounds Ia166.1–Ia166.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia167, inparticular to the compounds Ia167.1–Ia167.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia168, inparticular to the compounds Ia168.1–Ia168.64 which differ from compoundsIa1.1–Ia1.64 in that R² and R³ are chlorine, R¹³ is tert-butyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia169, inparticular to the compounds Ia169.1–Ia169.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R² and R³ are chlorine.

Particular preference is likewise given to the compounds Ia170, inparticular to the compounds Ia170.1–Ia170.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² and R³ are chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia171, inparticular to the compounds Ia171.1–Ia171.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² and R³ are chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia172, inparticular to the compounds Ia172.1–Ia172.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² and R³ are chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia173, inparticular to the compounds Ia173.1–Ia173.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R² and R³ are chlorine.

Particular preference is likewise given to the compounds Ia174, inparticular to the compounds Ia174.1–Ia174.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² and R³ are chlorine andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia175, inparticular to the compounds Ia175.1–Ia175.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² and R³ are chlorine andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia176, inparticular to the compounds Ia176.1–Ia176.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² and R³ are chlorine andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia177, inparticular to the compounds Ia177.1–Ia177.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is chlorine and R³ is methyl.

Particular preference is likewise given to the compounds Ia178, inparticular to the compounds Ia178.1–Ia178.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia179, inparticular to the compounds Ia179.1–Ia178.64 [sic] which differ fromcompounds Ia1.1–Ia1.64 in that R³ is methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia180, inparticular to the compounds Ia180.1–Ia180.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia181, inparticular to the compounds Ia181.1–Ia181.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia182, inparticular to the compounds Ia182.1–Ia182.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl, R¹³ is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia183, inparticular to the compounds Ia183.1–Ia183.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl, R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia184, inparticular to the compounds Ia184.1–Ia184.64 which differ from compoundsIa1.1–Ia1.64 in that R³ is methyl, R¹³ is tert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia185, inparticular to the compounds Ia185.1–Ia185.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl.

Particular preference is likewise given to the compounds Ia186, inparticular to the compounds Ia186.1–Ia186.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia187, inparticular to the compounds Ia187.1–Ia187.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia188, inparticular to the compounds Ia188.1–Ia188.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia189, inparticular to the compounds Ia189.1–Ia189.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl.

Particular preference is likewise given to the compounds Ia190, inparticular to the compounds Ia190.1–Ia190.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia191, inparticular to the compounds Ia191.1–Ia191.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia192, inparticular to the compounds Ia192.1–Ia192.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia193, inparticular to the compounds Ia193.1–Ia193.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R³ is methyl.

Particular preference is likewise given to the compounds Ia194, inparticular to the compounds Ia194.1–Ia194.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia195, inparticular to the compounds Ia195.1–Ia195.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia196, inparticular to the compounds Ia196.1–Ia196.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia97, inparticular to the compounds Ia197.1–Ia197.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia198, inparticular to the compounds Ia198.1–Ia198.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl and R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia199, inparticular to the compounds Ia199.1–Ia199.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl, R¹³ is isopropyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia200, inparticular to the compounds Ia200.1–Ia200.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is methyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia201, inparticular to the compounds Ia201.1–Ia201.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia202, inparticular to the compounds Ia202.1–Ia202.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is ethylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia203, inparticular to the compounds Ia203.1–Ia203.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is ethylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia204, inparticular to the compounds Ia204.1–Ia204.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is ethylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia205, inparticular to the compounds Ia205.1–Ia205.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia206, inparticular to the compounds Ia206.1–Ia206.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is ethylsulfonyl andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia207, inparticular to the compounds Ia207.1–Ia207.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is ethylsulfonyl andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia208, inparticular to the compounds Ia208.1–Ia208.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is ethylsulfonyl andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia209, inparticular to the compounds Ia209.1–Ia209.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R³ is methyl.

Particular preference is likewise given to the compounds Ia210, inparticular to the compounds Ia210.1–Ia210.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia211, inparticular to the compounds Ia211.1–Ia211.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia212, inparticular to the compounds Ia212.1–Ia212.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia213, inparticular to the compounds Ia213.1–Ia213.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia214, inparticular to the compounds Ia214.1–Ia214.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl, R¹³ is ethyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia215, inparticular to the compounds Ia215.1–Ia215.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl, R¹³ is isopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia216, inparticular to the compounds Ia216.1–Ia216.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R³ is methyl, R¹³ is tert-butyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia217, inparticular to the compounds Ia217.1–Ia217.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl and R² is chlorine.

Particular preference is likewise given to the compounds Ia218, inparticular to the compounds Ia218.1–Ia218.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is chlorine and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia219, inparticular to the compounds Ia219.1–Ia219.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is chlorine and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia220, inparticular to the compounds Ia220.1–Ia220.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R³ are methyl, R² is chlorine and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia221, inparticular to the compounds Ia221.1–Ia221.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R² is chlorine.

Particular preference is likewise given to the compounds Ia222, inparticular to the compounds Ia222.1–Ia222.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is chlorine and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia223, inparticular to the compounds Ia223.1–Ia223.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is chlorine and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia224, inparticular to the compounds Ia224.1–Ia224.64 which differ from compoundsIa1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is chlorine and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia225, inparticular to the compounds Ia225.1–Ia225.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl.

Particular preference is likewise given to the compounds Ia226, inparticular to the compounds Ia226.1–Ia226.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia227, inparticular to the compounds Ia227.1–Ia227.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia228, inparticular to the compounds Ia228.1–Ia228.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia229, inparticular to the compounds Ia229.1–Ia229.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia230, inparticular to the compounds Ia230.1–Ia230.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia231, inparticular to the compounds Ia231.1–Ia231.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia232, inparticular to the compounds Ia232.1–Ia232.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is methylsulfonyl, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia233, inparticular to the compounds Ia233.1–Ia233.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹² is methylsulfonyl.

Particular preference is likewise given to the compounds Ia234, inparticular to the compounds Ia234.1–Ia234.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is methylsulfonyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia235, inparticular to the compounds Ia235.1–Ia235.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is methylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia236, inparticular to the compounds Ia236.1–Ia236.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is methylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia237, inparticular to the compounds Ia237.1–Ia273.64 [sic] which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹² ismethylsulfonyl.

Particular preference is likewise given to the compounds Ia238, inparticular to the compounds Ia238.1–Ia238.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is methylsulfonyl andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia239, inparticular to the compounds Ia239.1–Ia239.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is methylsulfonyl andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia240, inparticular to the compounds Ia240.1–Ia240.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is methylsulfonyl andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia241, inparticular to the compounds Ia241.1–Ia241.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹² is methylsulfonyl.

Particular preference is likewise given to the compounds Ia242, inparticular to the compounds Ia242.1–Ia242.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia243, inparticular to the compounds Ia243.1–Ia243.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia244, inparticular to the compounds Ia244.1–Ia244.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia245, inparticular to the compounds Ia245.1–Ia245.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia246, inparticular to the compounds Ia246.1–Ia246.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl, R¹³ isethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia247, inparticular to the compounds Ia247.1–Ia247.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is methylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia248, inparticular to the compounds Ia248.1–Ia248.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is ethylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia249, inparticular to the compounds Ia249.1–Ia249.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹² ismethylsulfonyl.

Particular preference is likewise given to the compounds Ia250, inparticular to the compounds Ia250.1–Ia250.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia251, inparticular to the compounds Ia251.1–Ia251.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia252, inparticular to the compounds Ia252.1–Ia252.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia253, inparticular to the compounds Ia253.1–Ia253.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R¹²is methylsulfonyl.

Particular preference is likewise given to the compounds Ia254, inparticular to the compounds Ia254.1–Ia254.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia255, inparticular to the compounds Ia255.1–Ia255.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia256, inparticular to the compounds Ia256.1–Ia256.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹⁴ is tert-butyl.

Particular preference is likewise given to the compounds Ia257, inparticular to the compounds Ia257.1–Ia257.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹² is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia258, inparticular to the compounds Ia258.1–Ia258.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia259, inparticular to the compounds Ia259.1–Ia259.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia260, inparticular to the compounds Ia260.1–Ia260.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia261, inparticular to the compounds Ia261.1–Ia261.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl and R¹³ ismethyl.

Particular preference is likewise given to the compounds Ia262, inparticular to the compounds Ia262.1–Ia262.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia263, inparticular to the compounds Ia263.1–Ia263.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia264, inparticular to the compounds Ia264.1–Ia264.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia265, inparticular to the compounds Ia265.1–Ia265.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹² ismethylsulfonyl.

Particular preference is likewise given to the compounds Ia266, inparticular to the compounds Ia266.1–Ia266.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is methylsulfonyland R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia267, inparticular to the compounds Ia267.1–Ia267.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is methylsulfonyland R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia268, inparticular to the compounds Ia268.1–Ia268.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is methylsulfonyland R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia269, inparticular to the compounds Ia269.1–Ia269.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹² ismethylsulfonyl.

Particular preference is likewise given to the compounds Ia270, inparticular to the compounds Ia270.1–Ia270.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² ismethylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia271, inparticular to the compounds Ia271.1–Ia271.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² ismethylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia272, inparticular to the compounds Ia272.1–Ia272.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R³ ismethylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia273, inparticular to the compounds Ia273.1–Ia273.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia274, inparticular to the compounds Ia274.1–Ia274.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia275, inparticular to the compounds Ia275.1–Ia275.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia276, inparticular to the compounds Ia276.1–Ia276.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia277, inparticular to the compounds Ia277.1–Ia277.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia278, inparticular to the compounds Ia278.1–Ia278.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl, R¹³ is ethyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia279, inparticular to the compounds Ia279.1–Ia279.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl, R¹³ is isopropyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia280, inparticular to the compounds Ia280.1–Ia280.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is phenylsulfonyl, R¹³ is tert-butyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia281, inparticular to the compounds Ia281.1–Ia281.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹² is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia282, inparticular to the compounds Ia282.1–Ia282.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is phenylsulfonyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia283, inparticular to the compounds Ia283.1–Ia283.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is phenylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia284, inparticular to the compounds Ia284.1–Ia284.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is phenylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia285, inparticular to the compounds Ia285.1–Ia285.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹² is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia286, inparticular to the compounds Ia286.1–Ia286.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is phenylsulfonyl andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia287, inparticular to the compounds Ia287.1–Ia287.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is phenylsulfonyl andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia288, inparticular to the compounds Ia288.1–Ia288.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is phenylsulfonyl andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia289, inparticular to the compounds Ia289.1–Ia289.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹² is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia290, inparticular to the compounds Ia290.1–Ia290.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia291, inparticular to the compounds Ia291.1–Ia291.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia292, inparticular to the compounds Ia292.1–Ia292.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia293, inparticular to the compounds Ia293.1–Ia293.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia294, inparticular to the compounds Ia294.1–Ia294.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl, R¹³ isethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia295, inparticular to the compounds Ia295.1–Ia295.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia296, inparticular to the compounds Ia296.1–Ia296.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is phenylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia297, inparticular to the compounds Ia297.1–Ia297.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹² isphenylsulfonyl.

Particular preference is likewise given to the compounds Ia298, inparticular to the compounds Ia298.1–Ia298.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia299, inparticular to the compounds Ia299.1–Ia299.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia300, inparticular to the compounds Ia300.1–Ia300.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia301, inparticular to the compounds Ia301.1–Ia301.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl and R¹²is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia302, inparticular to the compounds Ia302.1–Ia302.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia303, inparticular to the compounds Ia303.1–Ia303.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia304, inparticular to the compounds Ia304.1–Ia304.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² isphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia305, inparticular to the compounds Ia305.1–Ia305.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹² is phenylsulfonyl.

Particular preference is likewise given to the compounds Ia306, inparticular to the compounds Ia306.1–Ia306.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl and R¹³ isethyl.

Particular preference is likewise given to the compounds Ia307, inparticular to the compounds Ia307.1–Ia307.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl and R¹³ isisopropyl.

Particular preference is likewise given to the compounds Ia308, inparticular to the compounds Ia308.1–Ia308.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia309, inparticular to the compounds Ia309.1–Ia309.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl and R¹⁴ ismethyl.

Particular preference is likewise given to the compounds Ia310, inparticular to the compounds Ia310.1–Ia310.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl, R¹³ is ethyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia311, inparticular to the compounds Ia311.1–Ia311.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl, R¹³ isisopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia312, inparticular to the compounds Ia312.1–Ia312.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is phenylsulfonyl, R¹³ istert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia313, inparticular to the compounds Ia313.1–Ia313.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹² isphenylsulfonyl.

Particular preference is likewise given to the compounds Ia314, inparticular to the compounds Ia314.1–Ia314.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is phenylsulfonyland R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia315, inparticular to the compounds Ia315.1–Ia315.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is phenylsulfonyland R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia316, inparticular to the compounds Ia316.1–Ia316.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is phenylsulfonyland R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia317, inparticular to the compounds Ia317.1–Ia317.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹² isphenylsulfonyl.

Particular preference is likewise given to the compounds Ia318, inparticular to the compounds Ia318.1–Ia318.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² isphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia319, inparticular to the compounds Ia319.1–Ia319.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² isphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia320, inparticular to the compounds Ia320.1–Ia320.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² isphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia321, inparticular to the compounds Ia321.1–Ia321.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia322, inparticular to the compounds Ia322.1–Ia322.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia323, inparticular to the compounds Ia323.1–Ia323.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia324, inparticular to the compounds Ia324.1–Ia324.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl and R¹³ istert-butyl.

Particular preference is likewise given to the compounds Ia325, inparticular to the compounds Ia325.1–Ia325.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia326, inparticular to the compounds Ia326.1–Ia326.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl, R¹³ is ethyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia327, inparticular to the compounds Ia327.1–Ia327.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl, R¹³ is isopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia328, inparticular to the compounds Ia328.1–Ia328.64 which differ from compoundsIa1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl, R¹³ is tert-butyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia329, inparticular to the compounds Ia329.1–Ia329.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl and R¹² is 4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia330, inparticular to the compounds Ia330.1–Ia330.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is 4-methylphenylsulfonyl and R¹³is ethyl.

Particular preference is likewise given to the compounds Ia331, inparticular to the compounds Ia331.1–Ia331.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is 4-methylphenylsulfonyl and R¹³is isopropyl.

Particular preference is likewise given to the compounds Ia332, inparticular to the compounds Ia332.1–Ia332.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R¹² is 4-methylphenylsulfonyl and R¹³is tert-butyl.

Particular preference is likewise given to the compounds Ia333, inparticular to the compounds Ia333.1–Ia333.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl and R¹² is4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia334, inparticular to the compounds Ia334.1–Ia334.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia335, inparticular to the compounds Ia335.1–Ia334.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia336, inparticular to the compounds Ia336.1–Ia336.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is4-methylphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia337, inparticular to the compounds Ia337.1–Ia337.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl and R¹² is4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia338, inparticular to the compounds Ia338.1–Ia338.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyland R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia339, inparticular to the compounds Ia339.1–Ia339.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyland R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia340, inparticular to the compounds Ia340.1–Ia340.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyland R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia341, inparticular to the compounds Ia341.1–Ia341.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia342, inparticular to the compounds Ia342.1–Ia342.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia343, inparticular to the compounds Ia343.1–Ia343.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyl,R¹³ is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia344, inparticular to the compounds Ia344.1–Ia344.64 which differ from compoundsIa1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² is 4-methylphenylsulfonyl,R¹³ is tert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia345, inparticular to the compounds Ia345.1–Ia345.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹² is4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia346, inparticular to the compounds Ia346.1–Ia346.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia347, inparticular to the compounds Ia347.1–Ia347.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia348, inparticular to the compounds Ia348.1–Ia348.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia349, inparticular to the compounds Ia349.1–Ia348.64 [sic] which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² isethylsulfonyl and R¹² is 4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia350, inparticular to the compounds Ia350.1–Ia350.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia351, inparticular to the compounds Ia351.1–Ia351.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia352, inparticular to the compounds Ia352.1–Ia352.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is ethylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia353, inparticular to the compounds Ia353.1–Ia353.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine and R¹² is 4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia354, inparticular to the compounds Ia354.1–Ia354.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl andR¹³ is ethyl.

Particular preference is likewise given to the compounds Ia355, inparticular to the compounds Ia355.1–Ia355.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl andR¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia356, inparticular to the compounds Ia356.1–Ia356.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl andR¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia357, inparticular to the compounds Ia357.1–Ia357.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia358, inparticular to the compounds Ia358.1–Ia358.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl, R¹³is ethyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia359, inparticular to the compounds Ia359.1–Ia359.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl, R¹³is isopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia360, inparticular to the compounds Ia360.1–Ia360.64 which differ from compoundsIa1.1–Ia1.64 in that R² is chlorine, R¹² is 4-methylphenylsulfonyl, R¹³is tert-butyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia361, inparticular to the compounds Ia361.1–Ia361.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹² is4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia362, inparticular to the compounds Ia362.1–Ia362.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia363, inparticular to the compounds Ia363.1–Ia363.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia364, inparticular to the compounds Ia364.1–Ia364.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia365, inparticular to the compounds Ia365.1–Ia365.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine and R¹² is4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia366, inparticular to the compounds Ia366.1–Ia366.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is ethyl.

Particular preference is likewise given to the compounds Ia367, inparticular to the compounds Ia367.1–Ia367.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is isopropyl.

Particular preference is likewise given to the compounds Ia368, inparticular to the compounds Ia368.1–Ia368.64 which differ from compoundsIa1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is tert-butyl.

Particular preference is likewise given to the compounds Ia369, inparticular to the compounds Ia369.1–Ia369.64 which differ from compoundsIa1.1–Ia1.64 in that R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia370, inparticular to the compounds Ia370.1 to Ia370.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia371, inparticular to the compounds Ia371.1 to Ia371.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia372, inparticular to the compounds Ia372.1 to Ia372.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R¹³ is cyclopropyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia373, inparticular to the compounds Ia373.1 to Ia373.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia374, inparticular to the compounds Ia374.1 to Ia374.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R¹³ is cyclopropyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia375, inparticular to the compounds Ia375.1 to Ia375.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia376, inparticular to the compounds Ia376.1 to Ia376.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R¹³ is cyclopropyl and R¹⁴is methyl.

Particular preference is likewise given to the compounds Ia377, inparticular to the compounds Ia377.1 to Ia377.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia378, inparticular to the compounds Ia378.1 to Ia378.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl, R¹³ is cyclopropyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia379, inparticular to the compounds Ia379.1 to Ia379.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl and R¹³is cyclopropyl.

Particular preference is likewise given to the compounds Ia380, inparticular to the compounds Ia380.1 to Ia380.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹³ iscyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia381, inparticular to the compounds Ia381.1 to Ia381.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R² isethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia382, inparticular to the compounds Ia382.1 to Ia382.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R² isethylsulfonyl, R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia383, inparticular to the compounds Ia383.1 to Ia383.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia384, inparticular to the compounds Ia384.1 to Ia384.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is ethylsulfonyl, R¹³is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia385, inparticular to the compounds Ia385.1 to Ia385.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia386, inparticular to the compounds Ia386.1 to Ia386.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine, R¹³ is cyclopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia387, inparticular to the compounds Ia387.1 to Ia387.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is chlorine and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia388, inparticular to the compounds Ia388.1 to Ia388.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹³ iscyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia389, inparticular to the compounds Ia389.1 to Ia389.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia390, inparticular to the compounds Ia390.1 to Ia390.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R² is chlorine,R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia391, inparticular to the compounds Ia391.1 to Ia391.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia392, inparticular to the compounds Ia392.1 to Ia392.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is chlorine, R¹³ iscyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia393, inparticular to the compounds Ia393.1 to Ia393.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is trifluoromethyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia394, inparticular to the compounds Ia394.1 to Ia394.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is trifluoromethyl, R¹³ is cyclopropyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia395, inparticular to the compounds Ia395.1 to Ia395.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ methyl, R² is trifluoromethyl and R¹³is cyclopropyl.

Particular preference is likewise given to the compounds Ia396, inparticular to the compounds Ia396.1 to Ia396.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is trifluoromethyl, R¹³is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia397, inparticular to the compounds Ia397.1 to Ia397.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R² are trifluoromethyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia398, inparticular to the compounds Ia398.1 to Ia398.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R² are trifluoromethyl, R¹³ iscyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia399, inparticular to the compounds Ia399.1 to Ia399.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia400, inparticular to the compounds Ia400.1 to Ia400.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methoxy, R² is trifluoromethyl, R¹³is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia401, inparticular to the compounds Ia401.1 to Ia401.64 which differ fromcompounds Ia1.1–Ia1.64 in that R³ is chlorine and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia402, inparticular to the compounds Ia402.1 to Ia402.64 which differ fromcompounds Ia1.1–Ia1.64 in that R³ is chlorine, R¹³ is cyclopropyl andR¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia403, inparticular to the compounds Ia403.1 to Ia403.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia404, inparticular to the compounds Ia404.1 to Ia404.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl, R³ is chlorine, R¹³is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia405, inparticular to the compounds Ia405.1 to Ia405.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R³ are methyl, R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia406, inparticular to the compounds Ia406.1 to Ia406.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia407, inparticular to the compounds Ia407.1 to Ia407.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R³ are methyl, R² is ethylsulfonyland R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia408, inparticular to the compounds Ia408.1 to Ia408.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² isethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia409, inparticular to the compounds Ia409.1 to Ia409.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R³ are methyl, R² is chlorine andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia410, inparticular to the compounds Ia410.1 to Ia410.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹, R³ and R¹⁴ are methyl, R² is chlorineand R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia411, inparticular to the compounds Ia411.1 to Ia411.64 which differ fromcompounds Ia1.1–Ia1.64 in that is R¹² methylsulfonyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia412, inparticular to the compounds Ia412.1 to Ia412.64 which differ fromcompounds Ia1.1–Ia1.64 in that is R¹² methylsulfonyl, R¹³ is cyclopropyland R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia413, inparticular to the compounds Ia413.1 to Ia413.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R¹² is methylsulfonyl andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia414, inparticular to the compounds Ia414.1 to Ia414.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ is methyl, R¹² ismethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia414, inparticular to the compounds Ia414.1 to Ia414.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia416, inparticular to the compounds Ia416.1 to Ia416.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is ethylsulfonyl, R¹² ismethylsulfonyl, R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia417, inparticular to the compounds Ia417.1 to Ia417.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is ethylsulfonyl, R¹² ismethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia418, inparticular to the compounds Ia418.1 to Ia418.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² isethylsulfonyl, R¹² is methylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia419, inparticular to the compounds Ia419.1 to Ia419.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl andR¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia420, inparticular to the compounds Ia420.1 to Ia420.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine, R¹² is methylsulfonyl,R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia421, inparticular to the compounds Ia421.1 to Ia421.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² ismethylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia422, inparticular to the compounds Ia422.1 to Ia422.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine,R¹² is methylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia423, inparticular to the compounds Ia423.1 to Ia423.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl and R¹³ iscyclopropyl.

Particular preference is likewise given to the compounds Ia424, inparticular to the compounds Ia424.1 to Ia424.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹² is 4-methylphenylsulfonyl, R¹³ iscyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia425, inparticular to the compounds Ia425.1 to Ia425.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R¹² is4-methylphenylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia426, inparticular to the compounds Ia426.1 to Ia426.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R¹² is4-methylphenylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia427, inparticular to the compounds Ia427.1 to Ia427.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia428, inparticular to the compounds Ia428.1 to Ia428.64 which differ fromcompounds Ia1.1–Ia1.64 in that R² is chlorine, R¹² is4-methylphenylsulfonyl, R¹³ is cyclopropyl and R¹⁴ is methyl.

Particular preference is likewise given to the compounds Ia429, inparticular to the compounds Ia429.1 to Ia429.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ is methyl, R² is chlorine, R¹² is4-methylphenylsulfonyl and R¹³ is cyclopropyl.

Particular preference is likewise given to the compounds Ia430, inparticular to the compounds Ia430.1 to Ia430.64 which differ fromcompounds Ia1.1–Ia1.64 in that R¹ and R¹⁴ are methyl, R² is chlorine,R¹² is 4-methylphenylsulfonyl and R¹³ is cyclopropyl.

The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I can beobtained by different routes, for example by the following processes:

Process A:

Reaction of pyrazoles of the formula II (where Z=H) with an activatedbenzoic acid IIIα or a benzoic acid IIIβ, which is preferably activatedin situ, to give the acylation product, followed by rearrangement.

L¹ is a nucleophilically displaceable leaving group, such as halogen,for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl,carboxylate, for example acetate, trifluoroacetate, etc.

The activated benzoic acid can be employed directly, as in the case ofthe benzoyl halides, or be generated in situ, for example usingdicyclohexylcarbodiimide, triphenylphosphane/azodicarboxylic acidesters, 2-pyridine disulfide/triphenylphosphane, carbonyldiimidazole,etc.

If appropriate, it may be advantageous to carry out the acylationreaction in the presence of a base. The reactants and the auxiliary baseare advantageously employed in equimolar amounts. A slight excess ofauxiliary base, for example from 1.2 to 1.5 molar equivalents, based onII, may be advantageous in some cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Suitable solvents are, for example, chlorinatedhydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane,dimethoxyethane, polar aprotic solvents, such as acetonitrile,dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate,or mixtures thereof.

If the activated carboxylic acid component used is a benzoyl halide, itmay be advantageous to cool the reaction mixture to 0–10° C. when addingthis reactant. The mixture is subsequently stirred at 20–100° C.,preferably at 25–50° C., until the reaction has gone to completion.Work-up is carried out in a customary manner, for example by pouring thereaction mixture into water and extracting the product of value.Solvents which are particularly suitable for this purpose are methylenechloride, diethyl ether and ethyl acetate. The organic phase is driedand the solvent removed, and the crude ester can then be used for therearrangement without further purification.

The rearrangement of the esters to the compounds of the formula I isadvantageously carried out at 20–40° C. in a solvent and in the presenceof a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride,1,2-dichloroethane, dioxane, dimethoxyethane, ethyl acetate, toluene ormixtures thereof. Preferred solvents are acetonitrile, dioxane anddimethoxyethane.

Suitable bases are tertiary amines, such as triethylamine, pyridine oralkali metal carbonates, such as sodium carbonate, potassium carbonate,which are preferably employed in equimolar amounts or in excess of up tofour times, based on the ester. Preference is given to usingtriethylamine or alkali metal carbonate, preferably in twice theequimolar ratio, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide,potassium cyanide, and organic cyano compounds, such as acetonecyanohydrin, trimethylsilyl cyanide. They are employed in an amount offrom 1 to 50 mole percent, based on the ester. Preference is given tousing acetone cyanohydrin or trimethylsilyl cyanide, for example in anamount of from 5 to 15, preferably 10, mole percent, based on the ester.

Work-up can be carried out in a manner known per se. The reactionmixture is, for example, acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5–10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the resulting precipitateis filtered off with suction and/or extracted with methylene chloride orethyl acetate, dried and concentrated. (Examples of the preparation ofesters of hydroxypyrazoles and the rearrangement of the esters aregiven, for example, in EP-A 282 944 and U.S. Pat. No. 4,643,757).

However, it may also be advantageous to generate the crude ester in situand to carry out the rearrangement without isolation or purification ofthe ester.

Process B:

Reaction of 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formulaI (where R¹²=H) with a compound of the formula V:

L² is a nucleophilically replaceable leaving groups, such as halogen,for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl,sulfonate.

The compounds of the formula V can be employed directly, such as, forexample, in the case of the sulfonyl halides, sulfonic anhydrides, or begenerated in situ, for example activated sulfonic acids (using sulfonicacid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc.).

The starting materials are generally employed in eguimolar amounts.However, it can also be advantageous to use an excess of one componentor the other.

If appropriate, it may be advantageous to carry out the reaction in thepresence of a base. The reactants and the auxiliary base are thenadvantageously employed in equimolar amounts. An excess of auxiliarybase, for example 1.5 to 3 molar equivalents, based on II, may beadvantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, such astriethylamine, pyridine, alkali metal carbonates, for example sodiumcarbonate, potassium carbonate, and alkali metal hydrides, for examplesodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene, chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide oresters, such as ethyl acetate, or mixtures thereof.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to afford theproduct.

The pyrazoles of the formula II (where R¹²=H) used as starting materialsare known or can be prepared by processes known per se (for example EP-A240 001 and J. Prakt. Chem. 315 (1973), 383).

3-(4,5-Dihydroisoxazol-5-yl)benzoic acid derivatives of the formula III

where:

-   R¹, R² are hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl,    C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl;-   R³ is hydrogen, halogen or C₁–C₆-alkyl;-   R⁴ is hydrogen or C₁–C₄-alkyl;-   R⁵, R⁶ are hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, di(C₁–C₄-alkoxy)-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)amino-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)aminoimino-C₁–C₄-alkyl, hydroxyimino-C₁–C₄-alkyl,    C₁–C₆-alkoxyimino-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,    C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,    C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,    C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,    di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the two    last-mentioned substituents may be partially or fully halogenated    and/or may carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;        or-   R⁵ and R⁶ together form a C₂–C₆-alkanediyl chain which may be mono-    to tetrasubstituted by C₁–C₄-alkyl and/or may be interrupted by    oxygen or an unsubstituted or C₁–C₄-alkyl-substituted nitrogen;-   R⁷ is halogen, cyano, hydroxyl, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, amino,    C₁–C₆-alkylamino, di(C₁–C₆-alkyl)amino, di(C₁–C₄-alkoxy)methyl,    hydroxyimino-C₁–C₄-alkyl, C₁–C₆-alkoxyimino-C₁–C₄-alkyl or COR⁸;-   R⁸ is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, hydroxyl,    C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy, C₁–C₄-haloalkoxy,    C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy or NR⁹R¹⁰;-   R⁹ is hydrogen or C₁–C₄-alkyl;-   R¹⁰ is C₁–C₄-alkyl;-   R¹⁵ is hydroxyl or a radical which can be removed by hydrolysis;    are novel.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals, which may be substituted,halides, hetaryl radicals which are attached via nitrogen, amino andimino radicals, which may be substituted, etc.

Preference is given to 3-(4,5-dihydroisoxazol-5-yl)benzoyl halides ofthe formula IIIα′ where L¹′=halogen (

III where R¹⁵=halogen)

where the variables R¹ to R⁷ are as defined under formula III and

-   L¹′ is halogen, in particular chlorine or bromine.

Preference is likewise given to 3-(4,5-dihydroisoxazol-5-yl)benzoicacids of the formula IIIβ (

III where R¹⁵=hydroxyl)

where the variables R¹ to R⁷ are as defined under formula III.

Preference is likewise given to 3-(4,5-dihydroisoxazol-5-yl)benzoicesters of the formula IIIγ (

III where R¹⁵=C₁–C₆-alkoxy)

where the variables R¹ to R⁷ are as defined under III and

-   L³ is C₁–C₆-alkoxy.

The particularly preferred embodiments of the3-(4,5-dihydroisoxazol-5-yl)benzoic acid derivatives of the formula IIIwith respect to the variables R¹ to R⁷ correspond to those of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I.

The 3-(4,5-dihydroisoxazol-5-yl)benzoyl halides of the formula IIIα′(where L¹′=Cl, Br) can be prepared in a manner known per se by reactingthe 3-(4,5-dihydroisoxazol-5-yl)benzoic acids of the formula IIIβ withhalogenating agents, such as thionyl chloride, thionyl bromide,phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.

The 3-(4,5-dihydroisoxazol-5-yl)benzoic acids of the formula IIIβ can beprepared in a known manner by acidic or basic hydrolysis from thecorresponding esters of the formula IIIγ (L³=C₁–C₆-alkoxy).

Likewise, the 3-(4,5-dihydroisoxazol-5-yl)benzoic acids of the formulaIIIβ can be obtained by reacting the corresponding halogen-substitutedcompounds of the formula VI (L⁴=Hal), in particular the iodine orbromine compounds, in the presence of a palladium, nickel, cobalt orrhodium transition metal catalyst and a base with carbon monoxide andwater under elevated pressure.

Furthermore, it is possible to convert, by Rosenmund-von Braun-reaction,compounds of the formula VI into the corresponding nitriles of theformula VII (cf., for example, Org. Synth. Vol. III (1955), 212), and toconvert these by subsequent hydrolysis into the compounds of the formulaIIIβ.

The compounds of the formulae VI and VII

where:

-   R¹, R² are hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl,    C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl;-   R³ is hydrogen, halogen or C₁–C₆-alkyl;-   R⁴ is hydrogen or C₁–C₄-alkyl;-   R⁵, R⁶ are hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, di(C₁–C₄-alkoxy)-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)amino-C₁–C₄-alkyl,    di(C₁–C₄-alkyl)aminoimino-C₁–C₄-alkyl, hydroxyimino-C₁–C₄-alkyl,    C₁–C₆-alkoxyimino-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,    C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,    C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,    C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,    di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the two    last-mentioned substituents may be partially or fully halogenated    and/or may carry one to three of the following groups:    -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or        C₁–C₄-haloalkoxy;        or-   R⁵ and R⁶ together form a C₂–C₆-alkanediyl chain which may be mono-    to tetrasubstituted by C₁–C₄-alkyl and/or may be interrupted by    oxygen or an unsubstituted or C₁–C₄-alkyl-substituted nitrogen;-   R⁷ is halogen, cyano, hydroxyl, C₁–C₆-alkyl, C₁–C₆-haloalkyl,    C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,    C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,    C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, amino,    C₁–C₆-alkylamino, di(C₁–C₆-alkyl)amino, di-(C₁–C₄-alkoxy)methyl,    hydroxyimino-C₁–C₄-alkyl, C₁–C₆-alkoxyimino-C₁–C₄-alkyl or COR⁸;-   R⁸ is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, hydroxyl,    C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy, C₁–C₄-haloalkoxy,    C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy or NR⁹R¹⁰;-   R⁹ is hydrogen or C₁–C₄-alkyl;-   R¹⁰ is C₁–C₄-alkyl;-   L⁴ is halogen;    are likewise novel.

The particular embodiments of the compounds of the formulae VI and VIIwith respect to the variables R¹ to R⁷ correspond to those of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I.

The esters of the formula IIIγ and the halogen compounds of the formulaVI can be prepared by 1,3-dipolar cycloaddition of nitrile oxides toappropriate alkenes of the formula VIII and IX, respectively.

The nitrile oxides are prepared in situ in a manner known per se.Suitable starting materials are, for example, aldoximes (cf., forexample, Houben-Weyl X5, p. 858ff.) or nitroalkanes (cf., for example,Houben-Weyl E5/2, p. 1594ff.). The synthesis the compounds of theformulae VIII and IX is known (cf., for example, WO 98/50337 or WO98/50366), or is carried out analogously to processes known from theliterature.

PREPARATION EXAMPLES4-[2-Chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole(Compound 2.8)

At 0–5° C., a solution of 6.7 g (20 mmol) of2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoylchloride in 80 ml of dimethoxyethane was added dropwise to a solution of2.0 g (20 mmol) of 5-hydroxy-1-methylpyrazole and 3.3 g (24 mmol) ofpotassium carbonate in 30 ml of anhydrous dimethoxyethane. After 12hours of stirring at room temperature, a further 8.2 g (60 mmol) ofpotassium carbonate were added, and the batch was refluxed for sixhours. After cooling, the reaction mixture was stirred into 1 l of waterand extracted with methylene chloride. The aqueous phase was thenadjusted to pH 4 using 10% strength hydrochloric acid and extractedrepeatedly with methylene chloride, with readjustment of the pH. Theorganic phase was dried and the solvent removed, giving 5.3 g (13 mmol,67%) of the desired compound.

M.p.: >215° C.

4-[2-Chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl]-5-hydroxy-1-cyclopropyl-1H-pyrazole(Compound 2.36)

At 0–5° C., a solution of 1.0 g (3 mmol) of2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoylchloride in 50 ml of dimethoxyethane was added dropwise to a solution of0.47 g (3 mmol) of 5-hydroxy-1-cyclopropylpyrazole and 0.5 g (3.6 mmol)of potassium carbonate in 36 ml of anhydrous dimethoxyethane. After 12hours of stirring at room temperature, a further 1.0 g (7.2 mmol) ofpotassium carbonate were added and the batch was refluxed for 6 hours.After cooling, the reaction mixture was stirred into 600 ml of water andextracted with methylene chloride. The aqueous phase was then adjustedto pH 4 using 10% strength hydrochloric acid and extracted withmethylene chloride. Drying of the organic phase and removal of thesolvent gave 0.8 g (1.8 mmol, 63%) of the desired compound.

M.p.: >220° C.

In addition to the compounds mentioned above, further derivatives of theformula I which were prepared or are preparable in an analogous mannerare listed in Table 2.

TABLE 2

Physical data No. R¹ R² R³ R⁵ R⁷ R¹² R¹³ R¹⁴ m.p. [° C.] 2.1 Cl Cl H HC(CH₃)₃ H CH₃ H 92–96 2.2 Cl SO₂CH₃ H H C(CH₃)₃ H CH₃ H 116–120 2.3 ClCl H H COOC₂H₅ H CH₃ H  98–104 2.4 Cl SO₂CH₃ H H COOCH₃ H CH₃ H 130–1352.5 Cl Cl H H COOH H CH₃ H  96–104 2.6 Cl Cl H H CH₃ H CH₃ H 83–98 2.7CH₃ SO₂CH₃ H H CH₃ H CH₃ H 216–223 2.8 Cl SO₂CH₃ H H CH₃ H CH₃ H >2152.9 Cl SO₂CH₃ H H CH₃ H CH(CH₃)₂ H 241–244 2.10 Cl Cl H CH₃ C(CH₃)₃ HCH₃ H 2.11 Cl Cl H CH₃ CH₃ H CH₃ H 2.12 Cl SO₂CH₃ H H CH(OC₂H₅)₂ H CH₃ H87–98 2.13 Cl SO₂CH₃ H H COCH₃ H CH₃ H 2.14 Cl SO₂CH₃ H OCH₃ CH₃ H CH₃ H2.15 Cl SO₂CH₃ H H Cl H CH₃ H 2.16 Cl SO₂CH₃ H H OCH₃ H CH₃ H 2.17 ClSO₂CH₃ H H SCH₃ H CH₃ H 2.18 Cl SO₂CH₃ H H SOCH₃ H CH₃ H 2.19 Cl SO₂CH₃H H SO₂CH₃ H CH₃ H 2.20 Cl SO₂CH₃ H H NH₂ H CH₃ H 2.21 Cl SO₂CH₃ H HNHCH₃ H CH₃ H 2.22 Cl SO₂CH₃ H H N(CH₃)₂ H CH₃ H 2.23 Cl SO₂CH₃ H H C₂H₅H CH₃ H 2.24 Cl SO₂CH₃ H H CH(CH₃)₂ H CH₃ H 2.25 Cl SO₂CH₃ H H CH₃CO(2-F—C₆H₄) CH₃ H 62–65 2.26 Cl SO₂CH₃ H H CH₃ H C₂H₅ H 230–231 2.27 ClSO₂CH₃ H H CH₃ H C(CH₃)₃ H 2.28 Cl SO₂CH₃ H H CH₃ H CH₃ CH₃ 2.29 CH₃SO₂CH₃ H H CH₃ H C₂H₅ H 213–215 2.30 CH₃ SO₂CH₃ H H CH₃ H CH(CH₃)₂ H217–221 2.31 CH₃ SO₂CH₃ H H CH₃ H C(CH₃)₃ H 210–213 2.32 CH₃ SO₂CH₃ H HCH₃ H CH₃ CH₃ 192–196 2.33 CH₃ SO₂CH₃ H H CH₃ CH₂—C₆H₅ CH₃ H Oil 2.34 ClSO₂CH₃ H H COOCH₃ CO(2-F—C₆H₄) CH₃ H Oil 2.35 CH₃ SO₂CH₃ H H CH(CH₃)₂ HCH₃ H 210–211 2.36 Cl SO₂CH₃ H H CH₃ H cyclo-C₃H₅ H >220 2.37 CH₃ SO₂CH₃H H CH(CH₃)₂ H CH(CH₃)₂ H 233–237 2.38 CH₃ SO₂CH₃ H H CH(CH₃)₂ H CH₃ CH₃180–183 2.39 Cl Cl H H CH₃ H CH₂CH₃ H 63–66 2.40 Cl Cl H H CH₃ H(CH₂)₂CH₃ H 205–208 2.41 Cl Cl H H CH₃ H CH₃ CH₃ 89–95 2.42 Cl Cl H HCH₃ H cyclo-C₃H₅ H 159–163 2.43 OCH₃ SO₂CH₃ H H CH₃ H CH₃ H 165–175 2.44OCH₃ SO₂CH₃ H H CH₃ H cyclo-C₃H₅ H 160–165 2.45 OCH₃ SO₂CH₃ H H CH₃ HCH(CH₃)₂ H 140–145 2.46 Cl Cl H H CH₃ CH₂—C₆H₅ CH₃ CH₃ 50–55 2.47 Cl ClH H CH₃ CH₂—C₆H₅ cyclo-C₃H₅ H oil 2.48 Cl Cl H H CH₃ CH₂—C₆H₅ CH₂CH₃ Hoil 2.49 Cl SO₂CH₃ H H CH₃ CH₂—C₆H₅ C(CH₃)₃ H 70–72 2.50 Cl SO₂CH₃ H HCH₃ CH₂—C₆H₅ CH(CH₃)₂ cyclo-C₃H₅ 76–82 2.51 Cl SO₂CH₃ H H CH₃ H CH(CH₃)₂CH(CH₃)₂ oil 2.52 Cl Cl H H CH₃ CH₂—C₆H₅ CH(CH₃)₂ H oil 2.53 CH₃ SO₂CH₃H H CH₃ H cyclo-C₃H₅ H 189–191 2.54 CH₃ SO₂CH₃ H H CH₃CH₂—CO(4-CH₃—C₆H₄) CH(CH₃)₂ H 148–150 2.55 Cl Cl H H CH₃ H CH₂CF₃ CH₃46–55 2.56 CH₃ SO₂CH₃ H H CH₃ SO₂-(4-CH₃—C₆H₄) CH(CH₃)₂ H 212–213 2.57CH₃ SO₂CH₃ H H CH₃ CH₂—C₆H₅ CH(CH₃)₂ H 91–95 2.58 Cl Cl H H CH₃ CH₂—C₆H₅CH₂CF₃ H oil 2.59 Cl Cl H H CH₃ H CH₂CF₃ H 75–80 2.60 Cl Cl H H CH₃CH₂—CO(4-CH₃—C₆H₄) cyclo-C₃H₅ H 70–75 2.61 Cl Cl H H CH₃SO₂-(4-CH₃—C₆H₄) cyclo-C₃H₅ H 67–75 2.62 CH₃ SO₂CH₃ H H CH₃CH₂-(3-thienyl) CH₃ H oil 2.63 CH₃ SO₂CH₃ H H CH₃ CH₂-(3-thienyl)CH(CH₃)₂ H 2.64 CH₃ SO₂CH₃ H H CH₃ CH₂C≡CH CH₃ H oil 2.65 CH₃ SO₂CH₃ H HCH₃ CH₂CO(4-CH₃—C₆H₄) CH₃ H 170–176 2.66 CH₃ SO₂CH₃ H H CH₃ CH₂—C₆H₅cyclo-C₃H₅ H 78–82 2.67 CH₃ SO₂CH₃ H H CH₃ CH₂-(3-thienyl) cyclo-C₃H₅ H

The syntheses of some starting materials are given below:

Methyl 2,4-dichloro-3-(3-tert-butyl-4,5-dihydroisoxazol-5-yl)benzoate

At room temperature, 17 ml of a 12% strength aqueous sodium hypochloritesolution were added dropwise with vigorous stirring to a solution of 2.6g (10 mmol) of methyl 2,4-dichloro-3-ethenylbenzoate and 1 g (10 mmol)of 2,2-dimethylpropionaldoxime in 100 ml of dichloromethane. Twice, ineach case after 2 hours of stirring, a further 0.5 g (5 mmol) of theoxime and 9 ml of the hypochlorite solution were added. The reactionmixture was stirred at room temperature for a further 12 hours and thenstirred into 350 ml of water. After extraction with dichloromethane,drying and removal of the solvent, the residue was chromatographed.

Yield: 1.5 g (45% of theory) of a yellow resin

Methyl2-chloro-3-(3-ethoxycarbonyl-4,5-dihydroisoxazol-5-yl)-4-methyl-sulfonylbenzoate

At room temperature, 6.4 ml (46 mmol) of triethylamine were slowly addeddropwise to a solution of 8.5 g (31 mmol) of methyl2-chloro-3-ethenyl-4-methylsulfonylbenzoate and 7.2 g (46 mmol) of ethyl2-chloro-2-hydroxyiminoacetate in 200 ml of dichloromethane. 3 furtherportions of in each case 4.8 g (31 mmol) of ethyl2-chloro-2-hydroxyiminoacetate and then 4.3 ml (31 mmol) oftriethylamine were added, in each case after 2 hours of stirring. Thereaction mixture was stirred at room temperature for another 12 hoursand then stirred into 600 ml of water. After extraction withdichloromethane, drying and removal of the solvent, the residue waschromatographed.

Yield: 5.7 g (47% of theory) of a clear resin.

2-Chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoicacid

-   a) Methyl    2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoate.    -   A spatula tip of 4-dimethylaminopyridine was added to a solution        of 40 g (145 mmol) of methyl        2-chloro-3-ethenyl-4-methylsulfonylbenzoate and 50 g (220 mmol)        of di-tert-butyl dicarbonate in 300 ml of acetonitrile, and 50 g        (640 mmol) of nitroethane were then slowly added dropwise. The        mixture was stirred at room temperature for 12 hours, and a        further 32.8 g (145 mmol) of di-tert-butyl dicarbonate and 22.9        g (290 mmol) of nitroethane were then added. After a further 12        hours, the solvent was distilled off and the residue was        digested with ethyl acetate. The mixture was filtered off with        suction, giving 32.1 g of the desired compound. A further 6.3 g        were obtained from the mother liquor after removal of the        solvent, followed by chromatography.

Yield: 39.4 g (82% of theory)

M.p.: 175° C.

-   b)    2-Chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoic    acid    -   69.4 g (174 mmol) of 10% strength aqueous sodium hydroxide        solution were added to a solution of 38.4 g (116 mmol) of methyl        2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoate        in 400 ml of methanol and 400 ml of tetrahydrofuran. The mixture        was stirred at room temperature for 12 hours, the solvent volume        was reduced to half of the original volume and the mixture was        poured into 1 l of water. Using 10% strength hydrochloric acid        the pH was adjusted to 1 and the resulting precipitate was        filtered off with suction.

Yield: 35.2 g (96% of theory)

M.p.: >220° C.

2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoicacid

-   a)    2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbromobenzene    -   A spatula tip of 4-dimethylaminopyridine was added to a solution        of 13.6 g (50 mmol) of        2-methyl-3-ethenyl-4-methylsulfonylbromobenzene and 16.7 g (74        mmol) of di-tert-butyl dicarbonate in 100 ml of acetonitrile,        and 17.9 g (229 mmol) of nitroethane were then slowly added        dropwise. The mixture was stirred at room temperature for 6        hours, and a further 11.1 g (50 mmol) of di-tert-butyl        dicarbonate and 7.8 g (100 mmol) of nitroethane were then added,        and the mixture was stirred at room temperature for 12 hours.        The solvent was removed and the residue was chromatographed.

Yield: 6.4 g (38% of theory)

-   b)    2-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoic    acid    -   6.4 g (19 mmol) of        2-methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbromobenzene        were dissolved in 65 ml of toluene and 30 ml of water and        admixed with 240 mg (1 mmol) of palladium acetate, 1.1 g (4        mmol) of tricyclohexylphosphane, 810 mg (19 mmol) of lithium        chloride and 5.4 ml (38 mmol) of triethylamine. The resulting        solution was then stirred in an autoclave at 140° C. and under a        carbon monoxide pressure of 20 bar for 36 hours. After cooling        and venting, insoluble components were filtered off and the        phases were separated. The organic phase was then extracted        twice with water containing a little triethylamine. The combined        aqueous phases were then adjusted to pH 1 using 10% hydrochloric        acid, and the resulting precipitate was filtered off.

Yield: 2.5 g (44% of theory)

M.p.: 199–205° C.

In addition to the compounds described above, Table 3 below listsfurther 3-(4,5-dihydroisoxazol-5-yl)benzoic acid derivatives of theformula III which are prepared or are preparable in a similar manner.

TABLE 3

Physical data No. R¹ R² R³ R⁵ R⁷ R¹⁵ [° C.] 3.1 Cl Cl H H CH₃ OCH₃ Resin3.2 Cl Cl H H CH₃ OH Resin 3.3 Cl Cl H H C(CH₃)₃ OCH₃ Resin 3.4 Cl Cl HH C(CH₃)₃ OH 3.5 Cl SO₂CH₃ H H C(CH₃)₃ OCH₃ 54–55 3.6 Cl SO₂CH₃ H HC(CH₃)₃ OH  97–100 3.7 Cl Cl H H COOEt OCH₃ Oil 3.8 Cl Cl H H COOEt OH3.9 Cl SO₂CH₃ H H COOEt OCH₃ Resin 3.10 Cl SO₂CH₃ H H COOEt OH 82–903.11 Cl Cl H H COOH OH 182–183 3.12 Cl Cl H H CF₃ OCH₃ Oil 3.13 Cl Cl HH CF₃ OH 3.14 Cl SO₂CH₃ H H CH₃ OCH₃   175 3.15 Cl SO₂CH₃ H H CH₃OH >220 3.16 CH₃ SO₂CH₃ H H CH₃ OCH₃ 120–121 3.17 CH₃ SO₂CH₃ H H CH₃ OH199–205 3.18 Cl SO₂CH₃ H H CH(OC₂H₅)₂ OCH₃ Resin 3.19 Cl SO₂CH₃ H HCH(OC₂H₅)₂ OH 3.20 Cl SO₂CH₃ H H CHO OCH₃ 3.21 Cl SO₂CH₃ H H CHO OH 3.22Cl Cl H CH₃ C(CH₃)₃ OCH₃ 3.23 Cl Cl H CH₃ C(CH₃)₃ OH 3.24 Cl Cl H HCOCH₃ OCH₃ 3.25 Cl Cl H H COCH₃ OH 3.26 Cl Cl H H Cl OCH₃ 3.27 Cl Cl H HCl OH

The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I andtheir agriculturally useful salts are suitable as herbicides, both inthe form of isomer mixtures and in the form of the pure isomers. Theherbicidal compositions comprising compounds of the formula I effectvery good control of vegetation on non-crop areas, especially at highrates of application. In crops such as wheat, rice, maize, soybeans andcotton they act against broad-leaved weeds and grass weeds withoutdamaging the crop plants substantially. This effect is observedespecially at low rates of application.

Depending on the application method in question, the compounds of theformula I, or herbicidal compositions comprising them, can additionallybe employed in a further number of crop plants for eliminatingundesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rusticaa),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Moreover, the compounds of the formula I can also be used in crops whichtolerate the action of herbicides due to breeding including geneticengineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be employed, for example, in the form of directlysprayable aqueous solutions, powders, suspensions, alsohighly-concentrated aqueous, oily or other suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for spreading orgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend on the intended purposes; in any case,they should guarantee the finest possible distribution of the activeingredients according to the invention.

The herbicidal compositions comprise a herbicidally active amount of atleast one compound of the formula I or of an agriculturally useful saltof I and auxiliaries conventionally used for the formulation of cropprotection products.

Suitable inert auxiliaries are essentially:

-   mineral oil fractions of medium to high boiling point such as    kerosene and diesel oil, furthermore coal tar oils and oils of    vegetable or animal origin, aliphatic, cyclic and aromatic    hydrocarbons, eg. paraffins, tetrahydronaphthalene, alkylated    naphthalenes and their derivatives, alkylated benzenes and their    derivatives, alcohols such as methanol, ethanol, propanol, butanol    and cyclohexanol, ketones such as cyclohexanone, strongly polar    solvents, for example amines such as N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles, as such or dissolved in anoil or solvent, can be homogenized in water by means of wetting agent,tackifier, dispersant or emulsifier. However, it is also possible toprepare concentrates composed of active substance, wetting agent,tackifier, dispersant or emulsifier and, if appropriate, solvent or oil,and these concentrates are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal, alkaline earthmetal and ammonium salts of aromatic sulfonic acids, for example ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, of alkyl- and alkylaryl sulfonates, of alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and of fatty alcohol glycol ether, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalenesulfonic acids, withphenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl, tributylphenyl polyglycolether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycolether acetate, sorbitol esters, lignin-sulfite waste liquors ormethylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orconcomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers. Solid carriers are mineral earths such as silicas,silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground synthetic material, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas andproducts of vegetable origin such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-useproducts can be varied within wide ranges. In general, the formulationscomprise approximately from 0.001 to 98% by weight, preferably 0.01 to95% by weight, of at least one active ingredient. The active ingredientsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The formulation examples below illustrate the preparation of suchproducts:

-   I. 20 parts by weight of the compound No. 2.7 are dissolved in a    mixture composed of 80 parts by weight of alkylated benzene, 10    parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1    mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium    dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40    mol of ethylene oxide and 1 mol of castor oil. Pouring the solution    into 100,000 parts by weight of water and finely distributing it    therein gives an aqueous dispersion which comprises 0.02% by weight    of the active ingredient.-   II. 20 parts by weight of the compound No. 2.7 are dissolved in a    mixture composed of 40 parts by weight of cyclohexanone, 30 parts by    weight of isobutanol, 20 parts by weight of the adduct of 7 mol of    ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of    the adduct of 40 mol of ethylene oxide and 1 mol of castor oil.    Pouring the solution into 100,000 parts by weight of water and    finely distributing it therein gives an aqueous dispersion which    comprises 0.02% by weight of the active ingredient.-   III. 20 parts by weight of the active ingredient No. 2.7 are    dissolved in a mixture composed of 25 parts by weight of    cyclohexanone, 65 parts by weight of a mineral oil fraction of    boiling point 210 to 280° C. and 10 parts by weight of the adduct of    40 mol of ethylene oxide and 1 mol of castor oil. Pouring the    solution into 100,000 parts by weight of water and finely    distributing it therein gives an aqueous dispersion which comprises    0.02% by weight of the active ingredient.-   IV. 20 parts by weight of the active ingredient No. 2.7 are mixed    thoroughly with 3 parts by weight of sodium    diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium    salt of a lignosulfonic acid from a sulfite waste liquor and 60    parts by weight of pulverulent silica gel and the mixture is ground    in a hammer mill. Finely distributing the mixture in 20,000 parts by    weight of water gives a spray mixture which comprises 0.1% by weight    of the active ingredient.-   V. 3 parts by weight of the active ingredient No. 2.7 are mixed with    97 parts by weight of finely divided kaolin. This gives a dust which    comprises 3% by weight of the active ingredient.-   VI. 20 parts by weight of the active ingredient No. 2.7 are mixed    intimately with 2 parts by weight of calcium    dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol    polyglycol ether, 2 parts by weight of the sodium salt of a    phenol/urea/formaldehyde condensate and 68 parts by weight of a    paraffinic mineral oil. This gives a stable oily dispersion.-   VII. 1 part by weight of the active ingredient No. 2.7 is dissolved    in a mixture composed of 70 parts by weight of cyclohexanone, 20    parts by weight of ethoxylated isooctylphenol and 10 parts by weight    of ethoxylated castor oil. This gives a stable emulsion concentrate.-   VIII. 1 part by weight of active ingredient No. 2.7 is dissolved in    a mixture composed of 80 parts by weight of cyclohexanone and 20    parts by weight of Wettol® EM 31 (=nonionic emulsifier based on    ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be applied pre- or post-emergence. If the activeingredients are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spray apparatus, in such a way that they come intoas little contact as possible, if any, with the leaves of the sensitivecrop plants while reaching the leaves of undesirable plants which growunderneath, or the bare soil (post-directed, lay-by).

Depending on the intended aim of the control measures, the season, thetarget plants and the growth stage, the application rates of thecompound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0kg/ha of active substance (a.s.).

To widen the spectrum of action and to achieve synergistic effects, the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I can bemixed and applied jointly with a large number of representatives ofother groups of herbicidally or growth-regulatory active ingredients.Suitable components in mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, aryloxy-/hetaryloxyalkanic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofuranes, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolcarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, in the form of amixture with additional other crop protection agents, for example withpesticides or agents for controlling phytopathogenic fungi or bacteria.Also of interest is the miscibility with mineral salt solutions whichare employed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates can also be added.

USE EXAMPLES

The herbicidal action of the3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended oremulsified in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with transparentplastic hoods until the plants had rooted. This cover caused uniformgermination of the test plants unless this was adversely affected by theactive ingredients.

For the post-emergence treatment, the test plants were grown to a plantheight of from 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. To this end, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rate of application for the post-emergencetreatment was 125 or 62.5 g/ha a.s. (active substance).

Depending on the species, the plants were kept at from 10 to 25° C. and20 to 35° C., respectively. The test period extended over 2 to 4 weeks.During this time, the plants were tended, and their response to theindividual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Scientific name Common name Avena fatua wild oat Bromus inermis bromeMatricaria wild chamomile chamomilla Matricaria inodora false chamomileTritricum aestivum spring wheat

At an application rate of 125 or 62.5 g/ha of a.s., the compound 2.7showed very good activity against the abovementioned harmful plants andwas compatible with spring wheat.

In contrast, at the same application rates, the comparative compound A(compound 20 from Table 1) known from WO 97/41118 caused damage in thecrop plant spring wheat, and had a weaker herbicidal activity againstthe harmful plants mentioned.

1. A 3(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I

where: R¹, R² are hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl,C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl; R³ is hydrogen, halogenor C₁–C₆-alkyl; R⁴ is hydrogen or C₁–C₄-alkyl; R⁵, R⁶ are hydrogen,halogen, cyano, nitro, C₁–C₄-alkyl, C₁–C₄-alkoxy-C₁–C₄-alkyl,di(C₁–C₄-alkoxy)-C₁–C₄-alkyl, di(C₁–C₄-alkyl)amino-C₁–C₄-alkyl,di(C₁–C₄alkyl)aminoimino-C₁–C₄-alkyl, hydroxyimino-C₁–C₄-alkyl,C₁–C₆-alkoxyimino-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the twolast-mentioned substituents may be partially or fully halogenated and/ormay carry one to three of the following groups: nitro, cyano,C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; or R⁵and R⁶ together form a C₂–C₆-alkanediyl chain which may be mono- totetrasubstituted by C₁–C₄-alkyl and/or may be interrupted by oxygen oran unsubstituted or C₁–C₄-alkyl-substituted nitrogen; R⁷ is halogen,cyano, hydroxyl, C₁–C₆-alkyl, C₁–C₆haloalkyl, C₁–C₆-alkoxy,C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio,C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,C₁–C₆-haloalkylsulfonyl, amino, C₁–C₆alkylamino, di(C₁–C₆-alkyl)amino,di(C₁–C₄-alkoxy)methyl, hydroxyimino-C₁–C₄-alkyl,C₁–C₆-alkoxyimino-C₁–C₄-alkyl or COR^(8;) R⁸ is hydrogen, C₁–C₄-alkyl,C₁–C₄-haloalkyl, hydroxyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,C₁–C₄-haloalkoxy, C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy or NR⁹R¹⁰; R⁹ ishydrogen or C₁–C⁴-alkyl; R¹⁰ is C₁–C₄-alkyl; R¹¹ is a pyrazole, attachedin the 4-position, of the formula II

where H¹² is hydrogen, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₃–C₄-alkenyl,C₃–C₄-alkynyl, C₁–C₄-alkylcarbonyl, C₁–C₄-haloalkylcarbonyl,C₁–C₄-alkylsulfonyl, C₁–C₄-haloalkylsulfonyl, thienylmethyl, phenyl,benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, wherethe phenyl radical of the five last-mentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl,C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹³ is C₁–C₆-alkyl, C₁–C₆-haloalkyl orC₃–C₆-cycloalkyl; R¹⁴ is hydrogen, C₁–C₆-alkyl or C₃–C₆-cycloalkyl; andits agriculturally useful salts.
 2. A3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimedin claim 1 where R³ is hydrogen.
 3. A3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimedin claim 1 where R¹, R² are nitro, halogen, cyano, C₁–C₆-alkyl,C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl.
 4. A3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimedin claim 1 where R¹² is C₁–C₄-alkylsulfonyl, C₁–C₄-halosulfonyl orphenylsulfonyl, where the phenyl radical may be partially or fullyhalogenated and/or may carry one to three of the following groups:nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy orC₁–C₄-haloalkoxy.
 5. A 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole ofthe formula I as claimed in claim 1 where R¹² is benzyl, where thephenyl radical may be partially or fully halogenated and/or may carryone to three of the following groups: nitro, cyano, C₁–C₄-alkyl,C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy.
 6. A3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimedin claim 1 where R¹² is hydrogen.
 7. A3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimedin claim 1 where R⁵ is hydrogen, halogen, cyano, nitro, C₁–C₄-alkyl,C₁–C₄-alkoxy-C₁–C₄-alkyl, C₁–C₄-alkoxycarbonyl-C₁–C₄-alkyl,C₁–C₄-alkylthio-C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-cyanoalkyl,C₃–C₈-cycloalkyl, C₁–C₄-alkoxy, C₁–C₄-alkoxy-C₂–C₄-alkoxy,C₁–C₄-haloalkoxy, C₁–C₄-alkylthio, C₁–C₄-haloalkylthio,di(C₁–C₄-alkyl)amino, COR⁸, phenyl or benzyl, where the two lastmentioned substituents may be partially or fully halogenated and/or maycarry one to three of the following groups: nitro, cyano, C₁–C₄-alkyl,C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄haloalkoxy; R⁶ is hydrogen orC₁–C₄-alkyl.
 8. A 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of theformula I as claimed in claim 1 where R⁵ and R⁶ are hydrogen.
 9. Aprocess for preparing 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles ofthe formula I as claimed in claim 1, which comprises acylating thepyrazole of the formula II where R¹²=H and where the variables R¹³ andR¹⁴ are as defined under claim 1

with an activated carboxylic acid IIIa or with a carboxylic acid IIIb,

where, the variables R¹ to R⁷ are as defined under claim 1 and L¹ is anucleophilically displaceable leaving group and rearranging theacylation product, if appropriate in the presence of a catalyst, to thecompounds I (where R¹²=H), followed, if desired, by reaction with acompound of the formula VL²-R¹² where R¹² is as defined under claim 1 except for hydrogen and L²is a nucleophilically displaceable leaving group, to prepare3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I whereR¹²≠hydrogen.
 10. A composition comprising a herbicidally effectiveamount of at least one 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole ofthe formula I or an agriculturally useful salt of I as claimed in claim1 and auxiliaries which are customary for formulating crop protectionagents.
 11. A process for preparing compositions as claimed in claim 10which comprises mixing a herbicidally effective amount of at least one3-(4,5-dihydroisoxazol-5-yl)-benzoylpyrazole of the formula I or anagriculturally useful salt of I and auxiliaries which are customary forformulating crop protection agents.
 12. A method for controllingundesirable vegetation, wherein a herbicidally effective amount of atleast one 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula Ior an agriculturally useful salts as claimed in claim 1 is allowed toact on plants, their habitat and/or seeds.